Triethylamine → (R)-(-)-1-CBZ-3-pyrrolidinol

HRID 50133

반응식

HRID 50133 반응식
[OH:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 2759337(R)-3-Pyrrolidinol

생성물 1

HCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

3-Hydroxy-(R)-pyrrolidine (8.71 g, 0.1 mol) was dissolved in CH2Cl2 (260 mL) and cooled to 0° C. Triethylamine (33.5 mL, 0.24 mol) and benzyl chloroformate (14.9 mL, 0.11 mol) were added, and the resulting solution was stirred for 2 h at 0° C. The solution was gradually warmed to room temperature and allowed to stir overnight. The solution was washed with 1 M HCl, saturated NaHCO3, and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate to afford 13.7 g (62% yield, 2 steps) of the desired product as a purple oil.

후처리

  1. temperatureThe solution was gradually warmed to room temperature
  2. stirringto stir overnight
  3. washThe solution was washed with 1 M HCl, saturated NaHCO3, and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-a01212e745274677b3fc30716fa73a7a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710186B2

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