Sodium Hydroxide → (4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

Participants

Reaction Steps

Methyl(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylate (5.00 g) was dissolved in methanol (30 mL). While stirring this solution under ice cooling, 5 mol/L aqueous sodium hydroxide (12 mL) was gradually added dropwise. After stirring at room temperature for 2 hours, the reaction mixture was evaporated under reduced pressure to remove methanol. The resulting residue was washed with diethyl ether, diluted with 10% aqueous potassium bisulfate (70 mL), and then extracted with ethyl acetate. The extracted solution was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Diisopropyl ether (20 mL) was added to the resulting residue and the precipitated crystal was collected by filtration to give the titled compound (3.91 g, white powder).

Provenance & Evidence