Benzyl chloroformate → Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate

HRID 338853노트

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HRID 338853 반응식
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.CCN(C(C)C)C(C)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>ClCCl>[C:9]([O:8][C:7]([NH:6][C@H:3]1[CH2:4][CH2:5][N:1]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:2]1)=[O:13])([CH3:10])([CH3:12])[CH3:11]

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

생성물 1

HCID 14555479Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate수율 97%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (6.0 g, 32.2 mmol) and DIEA (12.5 g, 16.8 mL, 96.6 mmol) in dichloromethane (60 mL) cooled to 0° C. on an ice-bath was added benzyl chloroformate (8.7 g, 7.2 mL, 48.3 mmol), and the resulting mixture stirred at 0° C. for 2 hours. The mixture was diluted with dichloromethane (30 mL) and washed successively with cold aqueous 10% HCl, water, saturated sodium bicarbonate solution and brine. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography silica gel (Biotage, 65M; 20% ethyl acetate/hexanes) to afford (S)-benzyl 3-(tert-butoxycarbonylamino)pyrrolidine-1-carboxylate (10 g, 97%).

후처리

  1. washwashed successively with cold aqueous 10% HCl, water, saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography silica gel (Biotage, 65M; 20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-fc7886ff83d540fdaf43f91d24d2c0bc
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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