Reaktion #43355

Reaktionsgleichung

2-fluoroethyl p-toluenesulfonate

Sodium hydride

DMF

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

→

title compound

Ausbeute 41.0%

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

Ausbeute 41.0%

Lösungsmittel

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle