(Diethylamino)sulfur trifluoride → (S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylate

HRID 15070

반응식

HRID 15070 반응식
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(=O)([O-])O.[Na+]>ClCCl>[F:7][CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

참가 물질

5

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 643448(S)-(-)-N-Boc-prolinol

생성물 1

HCID 86586409(S)-tert-Butyl 2-(fluoromethyl)pyrrolidine-1-carboxylate수율 12.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethylaminosulfur trifluoride (3.3 g, 20.5 mmols) was added to dichloromethane (30 mL) solution of tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (3.2 g, 15.9 mmols) under cooling with ice, and stirred at the same temperature for 6 hours. The reaction liquid was poured into saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. Then the organic layer 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 (C-300; ethyl acetate:hexane=1:20) to provide the title compound (390 mg, 12%).

후처리

  1. temperatureunder cooling with ice
  2. customThe reaction liquid
  3. extractionextracted with ethyl acetate
  4. washThen the organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentrating
  7. customthe reaction liquid under reduced pressure
  8. customthe residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20)

출처 및 근거

ORD 기록
ord-3516101f62994f8aab76601fa5fcc911
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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