反応 #43355

反応方程式

2-fluoroethyl p-toluenesulfonate

Sodium hydride

DMF

tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

→

title compound

収率 41.0%

tert-butyl (3R)-3-(2-fluoroethoxy)pyrrolidine-1-carboxylate

収率 41.0%

溶媒

Ethyl acetate

反応条件

後処理

1. 1
   workup.STIRRINGstirring at the same temperature
2. 2
   洗浄then was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   濃縮Concentrating the solvent under reduced pressure
5. 5
   その他the residue was purified on silica gel column chromatography (KP-Sil Sil FLASH 25+M, ethyl acetate:hexane=1:10→2:8)

実験手順

Sodium hydride (55% oiliness, 140 mg, 3.2 mmols) was added to DMF (5 mL) solution of tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate (501.2 mg, 2.7 mmols) and stirred at room temperature for 30 minutes, followed by addition of 2-fluoroethyl p-toluenesulfonate (1.17 g, 5.4 mmols) and further 24 hours' stirring at the same temperature. Ethyl acetate was added to the reaction liquid which then was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (KP-Sil Sil FLASH 25+M, ethyl acetate:hexane=1:10→2:8) to provide the title compound (253 mg, 41%).

出典