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

Participants

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)pyrrolidine-3(R)-carboxylic acid (800 mg, 3.72 mmol) in 20 mL of anhydrous THF was added dropwise BH3.THF complex (1M in THF, 7.4 mL, 2.0 equiv.) at 0° C. under N2. The resulting solution was stirred for 4 h at room temperature. The reaction was then quenched with water. The mixture was concentrated under vacuum and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was applied onto a silica gel column, which was eluted with EtOAc/petroleum ether 1:5 to give the title compound (720 mg, 96%) as a colorless oil. LC-MS (ESI) m/z 202 (M+H+).

Provenance & Evidence