Реакция #43348

Уравнение реакции

sodium hydrogencarbonate

Diethylaminosulfur trifluoride

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

→

title compound

Выход 12.1%

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

Выход 12.1%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураunder cooling with ice
2. 2
   ДругоеThe reaction liquid
3. 3
   Экстракцияextracted with ethyl acetate
4. 4
   ПромывкаThen the organic layer was washed with water and saturated brine
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   КонцентрированиеConcentrating
7. 7
   Другоеthe reaction liquid under reduced pressure
8. 8
   Другоеthe residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:20)

Методика

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%).

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