Toluene → N-[(S)-alpha-methylbenzyl]-(RS)-proline methyl ester

HRID 565721노트

반응식

HRID 565721 반응식
Br[CH:2]([CH2:7][CH2:8][CH2:9]Br)[C:3]([O:5][CH3:6])=[O:4].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][C@H:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH3:6][O:5][C:3](=[O:4])[CH:2]1[CH2:7][CH2:8][CH2:9][N:32]1[C@@H:25]([CH3:24])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 758181-Phenethylamine, (-)-HCID 10912698Methyl 2,5-dibromopentanoate

생성물 1

HCID 11160639N-[(S)-alpha-methylbenzyl]-(RS)-proline methyl ester수율 78.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Methyl (RS)-2,5-dibromovalerate (24.5 g) and toluene (19.8 g) were added to a 49% aqueous potassium carbonate solution (53.3 g), and heated to 80° C. (S)-α-methylbenzylamine (12.0 g) was added dropwise to the mixture obtained above at that temperature, and was stirred at that temperature for 9.5 hours. Water (33.9 g) was added to the reaction mixture, and then the organic layer was separated from the resulting mixture. Separated organic layer was washed with water, a 1% aqueous hydrochloric acid solution and water in this order, and concentrated under reduced pressure. Thus, N-[(S)-α-methylbenzyl]-(RS)-proline methyl ester (16.3 g) was obtained in a yield of 77.8%.

후처리

  1. additionwas added dropwise to the mixture
  2. customobtained above at that temperature
  3. customthe organic layer was separated from the resulting mixture
  4. washSeparated organic layer was washed with water
  5. concentrationa 1% aqueous hydrochloric acid solution and water in this order, and concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7af25a2137c0452f8a652c5f117e123a
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172234B2

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