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

HRID 60307노트

반응식

HRID 60307 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.N1C=CC=CC=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C(Cl)Cl.O>[C:9]([O:8][C:7]([NH:6][C@H:3]1[CH2:4][CH2:5][N:1]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:2]1)=[O:13])([CH3:10])([CH3:12])[CH3:11]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

생성물 1

HCID 14555479Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (4.2 g, 22 mmol) in methylene chloride (49 mL) was cooled at 0° C. and treated with pyridine (2.2 mL, 29 mmol) and benzyl chloroformate (3.8 mL, 29 mmol). The mixture was stirred at 0° C. for 30 minutes and then warmed to ambient temperature and stirred for 4 hours. The reaction mixture was diluted with water (100 mL) and methylene chloride (100 mL), the organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (silica, 40 g, ISCO, 1-100% ethyl acetate in heptanes) to afford the title compound as a white solid, which was used in the next step without any further purification (5.2 g, 73%).

후처리

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for 4 hours
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (silica, 40 g, ISCO, 1-100% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-09d563a7bcb14c8787418e340988d1a7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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