Reaktion #43348

Reaktionsgleichung

sodium hydrogencarbonate

Diethylaminosulfur trifluoride

tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

→

title compound

Ausbeute 12.1%

tert-butyl (2S)-2-(fluoromethyl)pyrrolidine-1-carboxylate

Ausbeute 12.1%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling with ice
2. 2
   SonstigeThe reaction liquid
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThen the organic layer was washed with water and saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   EinengenConcentrating
7. 7
   Sonstigethe reaction liquid under reduced pressure
8. 8
   Sonstigethe residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20)

Vorschrift

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%).

Quelle