(3R)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid → tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (1.21 g, 5.6 mmol) in THF (30 mL) at 0° C. was added borane THF (1.0 M, 17 mL, 16.9 mmol) dropwise. The resulting mixture was warmed to rt over 30 min and then heated at 45° C. for 1 h, then at 55° C. for 90 min. The reaction mixture was then cooled to 0° C. and quenched carefully with 3N HCl (30 mL). The resulting mixture was stirred at rt for 20 min before it was extracted with Et2O (50 mL). The organic layer was washed with sat. NaHCO3 (20 mL) brine (20 mL), dried over NaSO4, filtered, and concentrated under reduced pressure to give (R)-tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (1.1 g, 91%) as a colorless oil.

Provenance & Evidence