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CAS No. : | 161491-24-3 | MDL No. : | MFCD08752608 |
Formula : | C12H19NO5 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | HBWUTYLVFYVXML-UHFFFAOYSA-N |
M.W : | 257.28 | Pubchem ID : | 11276893 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; | EXAMPLE 98 Methyl 1-(2,4-dimethoxybenzoyl)-4-(3,1-benzoxazin-2-one-1-yl)-3-piperidine carboxylate STR118 Step 1: Methyl 4-oxo-3-piperidinecarboxylate hydrochloride (3.5 g, 18.1 mmol) was stirred in methylene chloride (30 mL) and treated is with di-t-butyl dicarbonate (3.6 g, 16.5 mmol) followed by triethylamine added dropwise to maintain the pH of the mixture (moistened E. Merck colorpHast sticks) in the range 7-8. The mixture was stirred at ambient temperature for 18 h, then washed with 1N HCl followed by saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness in vacuo to give methyl 1-Boc-4-oxo-3-piperidinecarboxylate. |
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