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

HRID 15070

反応式

HRID 15070 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-3516101f62994f8aab76601fa5fcc911
出典データセット
uspto-grants-2010_06
特許番号
US07732456B2

関連ノート

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