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

HRID 15070

Reaction equation

HRID 15070 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-3516101f62994f8aab76601fa5fcc911
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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