Acetyl chloride → (3S)-1-benzyl-3-acetoxypyrrolidine

HRID 15082

반응식

HRID 15082 반응식
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].C1COCC1.[CH2:17]([N:24]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[CH2:17]([N:24]1[CH2:28][CH2:27][C@H:26]([O:29][C:8](=[O:10])[CH3:9])[CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

생성물 1

HCID 15623663(3S)-1-benzyl-3-acetoxypyrrolidine수율 90%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Triethylamine (1.3 mL, 9.30 mmols) and acetyl chloride (0.6 mL, 8.46) were added to THF (20 mL) solution of (3S)-1-benzyl-3-hydroxypyrrolidine (1.5 g, 8.46 mmols) by the order stated, under cooling with ice, and stirred at the same temperature for an hour. Ethyl acetate was added to the reaction liquid which then was washed with water and saturated brine, and dried over anhydrous sodium sulfate. Concentrating the reaction liquid under reduced pressure, the residue was purified on silica gel column chromatography (KP—NH, ethyl acetate:hexane=1:20) to provide the title compound (1.68 g, 90%).

후처리

  1. temperatureunder cooling with ice
  2. washthen was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationConcentrating
  5. customthe reaction liquid under reduced pressure
  6. customthe residue was purified on silica gel column chromatography (KP—NH, ethyl acetate:hexane=1:20)

출처 및 근거

ORD 기록
ord-08c55e9d266e442688fef7b33c0e6450
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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