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[ CAS No. 146256-98-6 ] {[proInfo.proName]}

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Chemical Structure| 146256-98-6
Chemical Structure| 146256-98-6
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Product Details of [ 146256-98-6 ]

CAS No. :146256-98-6 MDL No. :MFCD06656201
Formula : C12H19NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :CWRFSVAKVCSOPI-UHFFFAOYSA-N
M.W : 257.28 Pubchem ID :10868942
Synonyms :

Safety of [ 146256-98-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 146256-98-6 ]

* 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 [ 146256-98-6 ]

[ 146256-98-6 ] Synthesis Path-Downstream   1~13

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  • [ 170123-25-8 ]
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YieldReaction ConditionsOperation in experiment
98.9% With sodium tetrahydroborate; In methanol; at 10℃; for 0.833333h; 4.2.2 tert-Butyl 3-ethyl 4-hydroxypyrrolidine-1,3-dicarboxylate 2a To a suspension of NaBH4 (2.74 g, 72.3 mmol) in anhydrous methanol (290 mL) was added 1a (37.19 g, 144.6 mmol) at below 10 °C. The reaction mixture was stirred at the same temperature for 50 min, and then 20percent aqueous acetic acid was added dropwise to adjust pH 7.0 at 0 °C, and then concentrated under reduced pressure. The residue was dissolved with ethyl acetate (400 mL), and washed with water (50 mL * 3), brine (40 mL * 2), dried over anhydrous sodium sulfate, and evaporated under vacuo to afford the title compound 2a (37.11 g, 98.9percent) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) delta (ppm): 4.53-4.42 (m, 1H), 4.16-4.08 (m, 2H), 3.36-3.60 (m, 2H), 3.43 (brs, 1H), 3.28-3.25 (brs, 2H), 3.01-2.97 (brs, 1H), 1.42 (s, 9H), 1.28-1.21 (m, 3H). MS-ESI (m/z): 282.75 (M + Na)+.
With sodium cyanoborohydride; In methanol; b) 4-Hydroxy-pyrrolidine-1,3-dicarboxylic acid 1-tert.-butylester 3-ethylester To a solution of 5.15 g (20 mmol) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester in 30 ml methanol was added 1.88 g (30 mmol) sodium cyanoborohydride and a small amount of methylorange. With stirring the pH was adjusted to 3 by dropwise addition of 1N hydrochloric acid (color change from yellow to orange). After no more acid was consumed the mixture was stirred for one hour. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed twice with water, then with brine, dried over magnesium sulfate and evaporated. The residual yellow oil was used in the next step without any further purification. GC/MS (HP 5890 II/HP 5972; column: HP 5, 30 m*25 mm*0.25 mum film thickness, carrier gas: helium, temperature gradient: 50° C., 3 min; then with 20° C./min to 250° C.;) tR=12.44 min (no separation of diastereomers) m/z [percent]=259 (M+,0.3), 241 (0.7), 202(5), 186 (7), 158 (10), 112 (14), 68 (31), 57 (100).
With sodium cyanoborohydride; In methanol; b 4-Hydroxy-pyrrolidine-1,3-dicarboxylic acid 1-tert.-butylester 3-ethylester To a solution of 5.15 g (20 mmol) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester in 30 ml methanol was added 1.88 g (30 mmol) sodium cyanoborohydride and a small amount of methylorange. With stirring the pH was adjusted to 3 by dropwise addition of 1N hydrochloric acid (color change from yellow to orange). After no more acid was consumed the mixture was stirred for one hour. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed twice with water, then with brine, dried over magnesium sulfate and evaporated. The residual yellow oil was used in the next step without any further purification. GC/MS (HP 5890 II/HP 5972; column: HP 5,30 m*25 mm*0.25 (m film thickness, carrier gas: helium; temperature gradient: 50 ° C., 3 min; then with 20 ° C./min to 250 ° C.;) tR =12.44 min (no separation of diastereomers) m/z [percent]=259 (M+,0.3), 241 (0.7), 202 (5), 186 (7), 158 (10), 112 (14), 68 (31), 57 (100).
  • 3
  • [ 2627-86-3 ]
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  • 4-(1-phenyl-ethylamino)-2,5-dihydro-pyrrole-1,3-dicarboxylic acid 1-<i>tert</i>-butyl ester 3-ethyl ester [ No CAS ]
  • 4
  • [ 3886-69-9 ]
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  • 4-(1-phenyl-ethylamino)-2,5-dihydro-pyrrole-1,3-dicarboxylic acid 1-<i>tert</i>-butyl ester 3-ethyl ester [ No CAS ]
  • 5
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  • [ 101385-93-7 ]
YieldReaction ConditionsOperation in experiment
10.8 g With 2,6-di-tert-butyl-4-methyl-phenol; In water; dimethyl sulfoxide; toluene; for 6h; Ethyl N-Boc pyrrolidonecarboxylate (20.0 g) (compound of formula (II) wherein R is Et) was dissolved in toluene (30 ml) and dimethylsulfoxide Mixture and 20 mg of 3,5-di-tert-butyl-4-hydroxytoluene (BHT) was added.The resulting mixture was heated to 115 ° C (internal temperature) and water (4.2 ml, 3.0 eq) was added dropwise over 5 h maintaining the internal temperature at 110-115 ° C.The desired conversion was achieved 1 hour after the water addition was completed.The reaction mixture was cooled to 20 ° C and diluted with water (10 ml).The layers were separated and the aqueous layer re-extracted with toluene (20 ml).The combined organic layers were washed with 20 ml of 5percent w / w aqueous NaCl and then with 10percent w / w NaCl (40 ml) and finally with 20 ml of water.The resulting toluene solution was treated with activated carbon.After filtration, the filtrate was concentrated to dryness to give an orange oil (14 g).Cyclohexane (12 ml) was added at -5 / -10 ° C and the resulting suspension was filtered and washed twice with 3.5 ml of cyclohexane.The solid was dried under vacuum in a 25 ° C oven to give 10.8 g of a white solidbody.The molar yield after separation was 75percent.
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  • [ 654638-73-0 ]
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YieldReaction ConditionsOperation in experiment
With ethanol; sodium;Reflux; The Preparation of Compound 14D: Sodium (27.6 g, 0.765 mol) was added stepwise to absolute ethanol (1.5 L). When the solid completely disappeared, compound 14C (300 g, 1.04 mol) was added to the solution. The reaction mixture was refluxed overnight, monitored with TCL (PE/EA=4:1), until the starting material was completely consumed. The reaction mixture was evaporated to remove most of the solvent. The residue was dissolved in water (1 L) and acidified with citric acid to pH 6. The mixture was extracted with EA (1 L×3). The extract liquors were combined, washed with brine (1 L×3), dried with anhydrous Na2SO4 and evaporated, to obtain compound 14D (169 g, 63.4percent) as a brown oily substance. The crude product was used directly in the next step without a further purification.
With sodium ethanolate; In ethanol;Reflux; Sodium ethoxide (27.6 g, 0.765 mol) was added stepwise to absolute ethanol (1.5 L). When the solid completely disappeared, compound 14C (300 g, 1.04 mol) was added to the solution. The reaction mixture was refluxed overnight, monitored with TCL (PE/EA=4:1), until the starting material was completely consumed. The reaction mixture was evaporated to remove most of the solvent. The residue was dissolved in water (1 L) and acidified with citric acid to pH 6. The mixture was extracted with EA (1 L×3). The extract liquors were combined, washed with brine (1 L×3), dried with anhydrous Na2SO4 and evaporated, to obtain compound 14D (169 g, 63.4percent) as a brown oily substance. The crude product was used directly in the next step without a further purification.
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  • (3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride [ No CAS ]
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  • [ 14719-37-0 ]
  • [ 140-88-5 ]
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YieldReaction ConditionsOperation in experiment
To a suspensionof sodium hydride (60 percent, 18.4 g, 768.47 mmol) in toluene (350 mL) at 0 °C was added portion wise Intermediate 11 (120 g, 591.13 mmol). After stirring for 5 h at this temperature, to the mixture was added drop wise ethyl acrylate (76.8 g, 768.47 mmol). After additional stirring for 2 h at rt, the reaction was quenched with water (200 mL) carefully and extracted with EtOAc (600 mL X 2). The combined extract was dried over anhydrous sodium sulfate, concentrated to afford crude Intermediate 12 (50 g, 33percent yield, pale brown liquid).JH NMR (400 MHz, CDCb)
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  • [ 74-88-4 ]
  • [ 897043-85-5 ]
YieldReaction ConditionsOperation in experiment
63% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 1.25h; To 4-oxo-pyrrolidine-1 ,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.02 g, 4.0 mmol) in THF at rt was added DBU (4.1 mmol). After 15 min, iodomethane (4.0 mmol) was added and the resultant mixture was stirred for 1 h. The mixture was concentrated and the resultant slurry was partitioned between chloroform and water. The aqueous portion was extracted twice and the combined organic solutions were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (4:1 hexanes/ethyl acetate) provided 677 mg (63percent) of the title compound as a colorless oil.
58.1% With potassium carbonate; In acetone; at 0 - 20℃; for 3.96667h; To a stirring solution of 1a (43.53 g, 169.2 mmol) dissolved inanhydrous acetone (846 mL) was added potassium carbonate(70.14 g, 507.6 mmol). Iodomethane (21.08 mL, 338.4 mmol) wasadded dropwise at 0 C for about 28 min. After the addition wascomplete, the reaction mixturewas stirred at the same temperaturefor 0.5 h and then allowed to stir for another 3 h at room temperature,and then filtered. The filtrate was concentrated under reducepressure at below 35 C to give a yellow oil. The residue was dissolvedwith dichloromethane (600 mL), and washed with water(100 mL 3), brine (80 mL 2), dried over anhydrous sodiumsulfate, and evaporated under vacuo. The residue was purified bycolumn chromatography (silica gel) eluted with petroleum etherand ethyl acetate (v: v 5: 1) to afford the title compound 1b(26.67 g, 58.1percent) as a pale yellow oil. 1H NMR (400 MHz, CDCl3)d (ppm): 4.28 (d, J 11.8 Hz, 1H), 4.19 (qd, J 7.1, 1.5 Hz, 2H), 4.05 (t,J 19.7 Hz, 1H), 3.81 (d, J 19.4 Hz, 1H), 3.47 (d, J 11.8 Hz, 1H),1.49 (s, 9H), 1.41 (s, 3H), 1.25 (t, J 7.1 Hz, 3H). MS-ESI (m/z): 289.13(M NH4).
32 g With potassium carbonate; In acetone; at 26℃; for 16h; To a solution of Intermediate 12 (50 g, 194.5 mmol) in acetone (500 mL), K2CO3 (53.6 g, 389.1 mmol) and methyl iodide (55.2 g, 389.1 mmol) were added slowly and stirred at 26 °C for 16 h. On completion, reaction mixture was filtered through celite and the filtrate was concentrated and purified by silica gel (100-200 mesh) columnchromatography (0-10percent EtOAc in petroleum ether as eluent) to afford Intermediate 13 (32 g, 60 percent Yield, pale yellow liquid).JH NMR (400MHz, CDCb) delta 4.27 (br d, J = 11.7 Hz, 1H), 4.19 (dq, J = 1.7, 7.1 Hz, 2H), 4.14-3.96 (m, 1H), 3.81 (d, J = 19.6 Hz, 1H), 3.46 (br d, J = 11.7 Hz, 1H), 1.49 (s, 9H), 1.41 (s, 3H), 1.29-1.22 (m, 3H).
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  • [ 946828-03-1 ]
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  • C20H36N2O6 [ No CAS ]
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