成人免费xx,国产又黄又湿又刺激不卡网站,成人性视频app菠萝网站,色天天天天

Home Cart Sign in  
Chemical Structure| 71486-53-8 Chemical Structure| 71486-53-8

Structure of 71486-53-8

Chemical Structure| 71486-53-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

{[proInfo.proName]}

CAS No.: 71486-53-8

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 71486-53-8 ]

CAS No. :71486-53-8
Formula : C7H12ClNO3
M.W : 193.63
SMILES Code : [H+].COC(=O)C1C(=O)CCNC1.[Cl-]
MDL No. :MFCD00012769
InChI Key :NMAACQILAGCQPR-UHFFFAOYSA-N
Pubchem ID :2724028

Safety of [ 71486-53-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 71486-53-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.71
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 47.7
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

55.4 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.17
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-3.93
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.27
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.59
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.69

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.02
Solubility 18.7 mg/ml ; 0.0965 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.89
Solubility 24.9 mg/ml ; 0.129 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.04
Solubility 17.6 mg/ml ; 0.091 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.36 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 2.03

Application In Synthesis of [ 71486-53-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 71486-53-8 ]

[ 71486-53-8 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 504-29-0 ]
  • [ 71486-53-8 ]
  • [ 111303-44-7 ]
  • 2
  • [ 1603-41-4 ]
  • [ 71486-53-8 ]
  • [ 111303-47-0 ]
  • 3
  • [ 695-34-1 ]
  • [ 71486-53-8 ]
  • [ 111303-46-9 ]
  • 4
  • [ 1603-40-3 ]
  • [ 71486-53-8 ]
  • [ 111303-45-8 ]
  • 5
  • [ 1072-98-6 ]
  • [ 71486-53-8 ]
  • [ 111303-49-2 ]
  • 6
  • [ 95-65-8 ]
  • [ 71486-53-8 ]
  • [ 63265-63-4 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 4 1,2,3,4-Tetrahydro-8,9-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one Prepared by the method described in Example 1 from 3,4-dimethylphenol (10.0 g, 0.082 moles) and methyl 4-oxo-3-piperdinecarboxylate hydrochloride (11.3 g, 0.058 moles). Recrystallization from 2-methoxyethanol yielded the product (11.2 g), mp 172°-l74° C.
  • 7
  • [ 150-19-6 ]
  • [ 71486-53-8 ]
  • [ 54504-36-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 8 1,2,3,4-Tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one Prepared by the method described for Example 1 from 3-methoxyphenol (16 g, 0.126 moles) and <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> (25 g, 0.129 moles). Recrystallization from ethanol gave the product (10.43 g), mp 179°-183° C.
  • 8
  • [ 533-31-3 ]
  • [ 71486-53-8 ]
  • [ 86370-95-8 ]
  • 10
  • [ 620-17-7 ]
  • [ 71486-53-8 ]
  • [ 86371-00-8 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 9 8-Ethyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-one Prepared by the method described for Example 1 from 3-ethylphenol (12.2 g, 0.1 moles) and <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> (19.3 g, 0.1 moles). The crude material is washed with water and dried to give the product (6.6 g), mp 80°-85° C.
  • 11
  • [ 5150-42-5 ]
  • [ 71486-53-8 ]
  • [ 86370-96-9 ]
  • 12
  • [ 642-71-7 ]
  • [ 71486-53-8 ]
  • [ 86370-97-0 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 3 1,2,3,4-Tetrahydro-8,9,10-trimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrochloride Prepared by the method described in Example 1 from 3,4,5-trimethoxyphenol (25 g, 0.14 moles) and <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> (18.8 g, 0.097 moles). Recrystallization from dilute aqueous hydrochloric acid yielded the product (17.5 g) as the hydrochloride, mp 232°-234° C.
  • 13
  • [ 618-45-1 ]
  • [ 71486-53-8 ]
  • [ 118514-03-7 ]
  • 14
  • [ 618-45-1 ]
  • [ 71486-53-8 ]
  • [ 86370-99-2 ]
  • 15
  • [ 5407-87-4 ]
  • [ 71486-53-8 ]
  • [ 111303-48-1 ]
  • 16
  • [ 16011-96-4 ]
  • [ 71486-53-8 ]
  • [ 111303-60-7 ]
  • 17
  • [ 54661-57-3 ]
  • [ 71486-53-8 ]
  • [ 111303-63-0 ]
  • 18
  • [ 17238-53-8 ]
  • [ 71486-53-8 ]
  • [ 134201-16-4 ]
  • 19
  • [ 76-83-5 ]
  • [ 71486-53-8 ]
  • [ 127956-05-2 ]
  • 20
  • [ 71486-53-8 ]
  • 1'-Carbamimidoyl-[1,4']bipiperidinyl-4'-carboxylic acid amide; compound with sulfuric acid [ No CAS ]
  • [ 134201-18-6 ]
  • 21
  • [ 71486-53-8 ]
  • 4-(4-Chloro-phenyl)-4-hydroxy-piperidine-1-carboxamidine; compound with sulfuric acid [ No CAS ]
  • [ 134201-17-5 ]
  • 22
  • [ 71486-53-8 ]
  • 2-imino-6-methylpiperidine hydrochloride [ No CAS ]
  • [ 111303-61-8 ]
  • 25
  • [ 71486-53-8 ]
  • [ 501-53-1 ]
  • [ 140176-27-8 ]
YieldReaction ConditionsOperation in experiment
85% With trimethylamine; In dichloromethane; at 0 - 25℃; for 2h; After cooling a mixture of the compound of formula FF (methyl 4-oxopipepidine-3- carboxylate hydrochloride, 5 0Og, 25 8mmol, Sigma-Aldpich) and TMA (9 0OmL, 64 6mmol, Sigma-Aldpich) in DCM (5OmL) to a temperature of 00C, benzyl carbonochlopidate (4 85g, 28 4mmol, Sigma-Aldpich) was added over a pepiod of lOmin After addition, the reaction mixture was stirred for lhr at a temperature of 00C, warmed to a temperature of about 25°C, and stirred for 1 hr more Thereafter, the reaction mixture was extracted with DCM/water The organic portion was separated, washed with 2N aqueous HCl, washed with saturated NaHCO3, washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to provide 6 38g of the compound of formula FG as a colorless oil (yield 85percent)The identity of the compound of formula FG, 1 -benzyl 3-methyl 4-oxopipepidine-l ,3- dicarboxylate, was confirmed using 1H NMRCompound FG 1H NMR deltaH (400MHz, CDCl,) 3 94-4 03 (m, 4H), 3 72 (s, 3H), 3 16-3 21 (m, IH), 3 02-3 09 (m, 2H), 2 85-2 92 (m, I H), 2 66-2 68 (m, IH), 1 99-2 06 (m, IH), 1 54-1 60 (m, IH)
43% With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; TEA (17.67 mL, 126.75 mmol) was added to a stirred solution of Methyl 4-oxo-3-piperidinecarboxylate hydrochloride (8.18 g, 42.25 mmol) in DCM (80 mL); the solution was cooled to 0 °C then benzyl chloroformate (6.93 mL, 48.58 mmol) was added dropwise. The resulting mixture was stirred at RT overnight. The mixture was washed with iN HCI aq then with aq. NaHCO3 saturated solution, organicphase was dried and concentrated under vacuum to give 1-benzyl 3-methyl 4-oxopiperidine-1,3- dicarboxylate (p142, 5.30 g, y= 43percent) as an orange oil.MS (ES) (m/z): 292.2 [M÷H]
43% With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; Preparation 12: 1-benzyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (P12) TEA (17.67 mL, 126.75 mmol) was added to a stirred solution of Methyl 4-oxo-3-piperidinecarboxylate hydrochloride (8.18 g, 42.25 mmol) in DCM (80 m L); the solution was cooled to 0 °C then benzyl chloroformate (6.93 mL, 48.58 mmol) was added dropwise. The resulting mixture was stirred at RT overnight. The mixture was washed with IN HCI aq then with aq. Na HC03saturated solution, organic phase was dried and concentrated under vacuum to give 1-benzyl 3-methyl 4-oxopiperidine-l,3- dicarboxylate (pl2, 5.30 g, y= 43percent) as an orange oil.MS (ES) (m/z): 292.2 [M+H]+.
With N-ethyl-N,N-diisopropylamine; This compound may be prepared in the same manner as ethyl 1-benzoyl-3-piperidinecarboxylate, starting with commercially available <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong>, diisopropylethylaamine and commercially available benzyl chloroformate.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 15.5h; Methyl 4-oxopiperidine-3-carboxylate hydrochloride (25 g, 129.11 mmol) was suspended in DCM (250 mL) at 0°C and DIPEA (38.4 g, 297 mmol, 50.8 mL) was added slowly to give a clear solution. CbzCI (24.2 g, 142 mmol, 20.3 mL) was then added dropwise to the solution and stirred at 0°C for 30 min and then at rt for another 15 h for full conversion of the starting amine. The reaction mixture was washed with 10percent aq. citric acid (2 x 100 mL), dried (MgSC>4), filtered and concentrated in vacuo to provide intermediate 1 (39.8 g, 123 mmol, 95percent yield) as a crude yellow oil pure enough for further manipulation.UPLC-MS: tR= 0.78 (M+H+) = 293.31H NMR (300 MHz, Chloroform-d) delta 11.97 (s, 1H), 7.46 - 7.27 (m, 5H), 5.16 (s, 2H), 4.14 (t, J = 1.7 Hz, 2H), 3.78 (s, 3H), 3.65 (t, J = 6.0 Hz, 2H), 2.39 (br s, 2H).

  • 26
  • [ 71486-53-8 ]
  • [ 143-37-3 ]
  • [ 134201-14-2 ]
  • 27
  • [ 71486-53-8 ]
  • [ 79-22-1 ]
  • [ 31633-70-2 ]
  • 28
  • [ 71486-53-8 ]
  • [ 618-39-3 ]
  • [ 134201-15-3 ]
  • 29
  • [ 71486-53-8 ]
  • [ 108-95-2 ]
  • [ 59456-02-9 ]
  • 31
  • [ 24424-99-5 ]
  • [ 71486-53-8 ]
  • [ 161491-24-3 ]
YieldReaction ConditionsOperation in experiment
100% With sodium carbonate; In tetrahydrofuran; water; at 0℃; for 1h; Methyl 4-oxopiperidine-3-carboxylate hydrochloride (10.0 g, 51.6 mmol, 1 eq.) was dissolved in water (60 mL) at room temperature then cooled to 0° C. Added sodium carbonate (6.02 g, 56.8 mmol, 1.05 eq.) followed by the dropwise addition of BOC anhydride (11.84 g, 51.6 mmol, 1 eq.) in THF (50 mL) via an addition funnel. Stirred at 0° C. for 1 hour. Worked up by extracting 3 times with diethyl ether (50 mL). The diethyl ether extracts were combined and rinsed once (50 mL) with brine. The diethyl ether layer was dried over sodium sulfate and stripped to give 1-tert-butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (13.29 g) as an amber oil. Yield=100percent. 1H NMR (400 MHz) (CDCl3) delta 4.02 (s, 2H); 3.77 (s, 3H); 3.59 (s, 2H); 2.37 (s, 2H); 1.47 (s, 9H).
100% Compound 13 (25.0 g, 0.129 mol), di-t-butyl dicarbonate (33.8 g, 0.155 mol), and Et3N (26.1 g, 36.0 ml, 0.258 mol) were combined in CH2Cl2 (240 ml) and MeOH (60 ml), stirred at 23° C. for 16 h and concentrated. 1.0 N NaOH (100 ml) was added and the mixture extracted with CH2Cl2. The combined organic extracts were dried (MgSO4), filtered, and concentrated. Purification by silica gel chromatography (eluant: 5percent EtOAc-hexane, to 10percent EtOAc-hexane) gave 33.2 g (0.129 mol, 100percent) of the product 14 as a colorless oil. MS (FAB for M+1): m/e 258.
99% With triethylamine;dmap; In dichloromethane; at 20℃; for 2h;Product distribution / selectivity; Methyl 4-oxo-3-piperidinecarboxylate hydrochloride (5 g, 25.82 mmol) was dissolved in dichloromethane (50 rnL) and triethylamine (3.60 mL, 25.82 mmol). Di-te/t-butyl dicarbonate (5.93 mL, 25.82 mmol) was carefully added and the reaction mixture was stirred at room temperature for 2h. The reaction mixture was washed with 2M HCl (aq.) and brine. The organic phase was dried under MgSO4 and concentrated under reduced pressure yielding 3-methyl 4-oxopiperidine-l,3-dicarboxylate (6.55 g, 99 percent). MS (ES+) m/z 256.1 (M-H)-IH NMR (400 MHz, CHLOROFORM-J) delta ppm 1.48 (s, 9 H) 1.49 (s, 3 H) 2.38 (t, 2 H) 3.57 (t, 2 H) 3.77 (s, 1 H) 3.78 (s, 3 H) 4.06 (br. s., 2 H) 11.98 (s, 1 H)
99% A mixture of 20 gm (103.3 mMol) <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> and 75 mL saturated aqueous sodium bicarbonate in 150 mL dichloromethane was stirred vigorously at room temperature. A solution of 24.8 gm (113.6 mMol) di-tert-butyl dicarbonate in 100 mL dichloromethane was then added dropwise over three hours. After stirring at room temperature for about 16 hours, an additional 3.0 gm di-tert-butyl dicarbonate were added and stirring continued for an additional 2 hours. The reaction mixture was then diluted with water and extracted with 2 x 250 mL dichloromethane. The organic phases were combined, dried over magnesium sulfate, and concentrated under reduced pressure to provide 26.2 gm (99percent) of the desired compound as a yellow oil.
99% With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 21h; A mixture of 20 gm (103.3 MMol) <strong>[71486-53-8]methyl 4-oxo-3-piperidinecarboxylate hydrochloride</strong> and 75 ML saturated aqueous sodium bicarbonate in 150 ML dichloromethane was stirred vigorously at room temperature.. A solution of 24.8 gm (113.6 MMol) di-tert-butyl dicarbonate in 100 ML dichloromethane was then added dropwise over three hours.. After stirring at room temperature for about 16 hours, an additional 3.0 gm di-tert-butyl dicarbonate were added and stirring continued for an additional 2 hours.. The reaction mixture was then diluted with water and extracted with 2 x 250 ML dichloromethane.. The organic phases were combined, dried over magnesium sulfate, and concentrated under reduced pressure to provide 26.2 gm (99percent) of the desired compound as a yellow oil.
93% With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20℃; for 16h; A. 1-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate (34a1) Methyl 4-oxo-3-piperidine-carboylate hydrochloride (5 g, 30.2 mmol) was suspended in 60 mL THF and charged with Boc anhydride (6.6 g, 30.2 mmol) and sodium bicarbonate 2N aqueous solution (60 mL, 4.0 mmol) at 0° C. The reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was washed with water (2*30 mL) and brine (40 mL), dried over Na2SO4 and concentrated in vacuo to afford the title compound as colorless oil (9 g, 93percent). MS (ES-): m/z=256 (M-1) 1H NMR (400 MHz, CHLOROFORM-D) delta=1.48 (s, 9H) 2.37 (t, J=5.81 Hz, 2H) 2.60-2.63 (m, 1H) 3.56 (t, J=5.81 Hz, 2H) 3.78 (s, 3H) 4.05 (s, 2H)
76% With dmap; In dichloromethane; at 20℃; for 16h; To an ice-cold solution of <strong>[71486-53-8]methyl 4-oxopiperidine-3-carboxylate hydrochloride</strong> (1 g, 5.18 mmol) in DCM (10 mL) was added DMAP (1.2 g, 10.36 mmol) followed by addition of Boc anhydride (1 mL, 5.18 mmol). The mixture was stirred at rt for 16 h. After completion of reaction (by TLC), DCM (75 mL) was added and the organic layer washed with water and brine then dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 10percent EtOAc: hexane to obtain the product as a viscous liquid (1.30 g, 76percent yield). MS: 258.32 [M+H]+.
With triethylamine; In dichloromethane; To a cold (0° C.) mixture of 3-methoxycarbonyl 4-piperidone HCl (10 g, 51.6 mmol) and triethylamine (10.8 mL, 77.5 mmol) in dichloromethane (100 mL) was added a solution of di-tert-butyl dicarbonate (11.8 g, 54.2 mmol) in dichloromethane (100 mL). The mixture was stirred at room temperature for 2 hrs and concentrated under reduced pressure. The residue was quenched with water, extracted with ether, dried over MgSO4, filtered, and evaporated to give 1-tert-butyl 3-methyl 4-oxo-1,3-piperidinedicarboxylate, which was used for the next reaction without further purification. (14.9 g, yield; quant.)
With triethylamine; In methanol; ethyl acetate; Part C. Preparation of 1-t-butyloxycarbonyl-3-carbomethoxy-4-piperidone. Methyl 4-piperidone-3-carboxylate hydrochloride (25.09 g, 130 mmol, 1 eq) was dissolved in methanol. Triethylamine (18.10 mL, 130 mmol, 1 eq) was added followed by di-t-butyldicarbonate (28.28 g, 130 mmol, 1 eq) all at 0° C. (Note: rapid CO2 evolution). The mixture was stirred overnight at room temperature. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate, and washed with 10percent citric acid (3 X) and once with brine. The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield 24.62 g of an amber oil. NMR (CDCl3) delta811.97 (s, 1H); 4.05 (m, 2H); 3.78 (s, 3H); 3.57 (t, 2H, J=7 Hz); 2.38 (bt, 2H, J=7 Hz); 1.47 (s, 9H).
With triethylamine; In dichloromethane; at 0 - 20℃; for 4h; Preparation 28: 1-(1,1-dimethylethyl) 3-methyl 4-oxo-1,3-piperidinedicarboxylate (P28)To an ice cooled suspension of methyl 4-oxo-3-pipehdinecarboxylate hydrochloride (15.01 g) in dichloromethane (250 mL) was added bis(1 ,1-dimethylethyl) dicarbonate (17.76 g), then triethylamine (27 mL) was added dropwise. The resulting mixture was allowed to reach room temperature and stirred for 4 h. Saturated NH4CI was poured into the reaction <n="100"/>mixture and the phases were separated, the organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. Diethylether was added to the residue and filtered over a celite pad. The solvent was removed under reduced pressure to obtain the title compound (16.96 g). MS (m/z): 258 [MH]+, 202 [MH-56]+.
With triethylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 1h; General procedure: A stirred solution of ethyl 4-oxopiperidine-3-carboxylate hydrochloride 55a (3.38 g,16.3 mmol) and triethylamine (5.0 mL, 35.9 mmol) in dichloromethane (50 mL) and tetrahydrofuran (10 mL) is treated dropwise with a solution of di-tert-butyl dicarbonate in tetrahydrofuran (18 mL, 18 mmol) and the mixture is stirred at room temperature for 1 hour. The mixture is concentrated in vacuo, the residue is dissolved in dichloromethane and the organic phase is washed with sat. NaHCO3 solution and water, dried over Na2SO4 and concentrated to yield 1-tert-butyl 3-ethyl 4-oxopiperidine-1,3-dicarboxylate 55b as a clear oil.
With triethylamine; In dichloromethane; at 20℃; for 12h; Step 1 4-Oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester To a solution of di-tert-butyl-dicarbonate (3.08 g, 14.1 mmol) in CH2Cl2 (134 mL) was added methyl-4-oxo-3-piperidine carboxylate HCl (2.6 g, 13.4 mmol) and triethylamine (3.84 mL, 27.5 mmol). The solution was stirred at rt for 12 h. Gas evolution was observed. The reaction was quenched with 1N HCl and extracted with CH2Cl2 (3*), and the organic layers were collected together, dried over MgSO4 and evaporated in vacuo. The residue was purified to yield the title compound as a colorless oil. 1H-NMR (CDCl3) delta: 1.46 (s, 9H), 2.36 (t, 2H), 3.55 (t, 2H), 3.77 (s, 4H), 4.04 (s, 2H).

  • 32
  • [ 71486-53-8 ]
  • [ 98-09-9 ]
  • [ 566905-25-7 ]
 

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 71486-53-8 ]

Esters

Chemical Structure| 89895-55-6

A122799 [89895-55-6]

Methyl piperidine-3-carboxylate hydrochloride

Similarity: 0.91

Chemical Structure| 164323-84-6

A129793 [164323-84-6]

(S)-Methyl piperidine-3-carboxylate hydrochloride

Similarity: 0.91

Chemical Structure| 19673-14-4

A143668 [19673-14-4]

Ethyl 5-oxoazepane-4-carboxylate hydrochloride

Similarity: 0.89

Chemical Structure| 50585-89-2

A234386 [50585-89-2]

Methyl piperidine-3-carboxylate

Similarity: 0.88

Chemical Structure| 2044704-66-5

A371265 [2044704-66-5]

Methyl 4-hydroxypiperidine-3-carboxylate hydrochloride

Similarity: 0.87

Ketones

Chemical Structure| 19673-14-4

A143668 [19673-14-4]

Ethyl 5-oxoazepane-4-carboxylate hydrochloride

Similarity: 0.89

Chemical Structure| 72738-09-1

A509822 [72738-09-1]

Ethyl 3-oxopiperidine-4-carboxylate hydrochloride

Similarity: 0.83

Chemical Structure| 3939-01-3

A123040 [3939-01-3]

Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Similarity: 0.73

Chemical Structure| 1454-53-1

A211648 [1454-53-1]

Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Similarity: 0.70

Chemical Structure| 10420-33-4

A113066 [10420-33-4]

Dimethyl acetylsuccinate

Similarity: 0.67

Related Parent Nucleus of
[ 71486-53-8 ]

Piperidines

Chemical Structure| 89895-55-6

A122799 [89895-55-6]

Methyl piperidine-3-carboxylate hydrochloride

Similarity: 0.91

Chemical Structure| 164323-84-6

A129793 [164323-84-6]

(S)-Methyl piperidine-3-carboxylate hydrochloride

Similarity: 0.91

Chemical Structure| 50585-89-2

A234386 [50585-89-2]

Methyl piperidine-3-carboxylate

Similarity: 0.88

Chemical Structure| 2044704-66-5

A371265 [2044704-66-5]

Methyl 4-hydroxypiperidine-3-carboxylate hydrochloride

Similarity: 0.87

Chemical Structure| 4842-86-8

A200290 [4842-86-8]

Ethyl 3-piperidinecarboxylate hydrochloride

Similarity: 0.87