(3R,4S)-tert-butyl 3-(benzyloxycarbonylamino)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate → Benzyl (3r,4s)-4-hydroxypyrrolidin-3-ylcarbamate

Participants

Reaction Steps

A solution of (3R,4S)-tert-butyl 3-(benzyloxycarbonylamino)-4-(bis(4-methoxyphenyl)(phenyl)methoxy)pyrrolidine-1-carboxylate (2.18 g, 3.14 mmol) was stirred in a 10% TFA/dichloromethane solution (30 mL) for 30 minutes. The solution was concentrated under reduced pressure and the residue dissolved in ethyl acetate (15 mL) and treated with 2N HCl-diethyl ether (30 mL) for 1 hour. The resulting precipitate was collected by filtration and washed with ethyl acetate and dried to an off-white solid. The solid was dissolved in a 50% MeOH:dichloromethane solution (30 mL) and stirred with solid sodium carbonate (5 g) for 2.5 hours. The solids were collected by filtration and washed with 50% MeOH/dichloromethane solution and the filtrate concentrated under reduced pressure to give benzyl (3R,4S)-4-hydroxypyrrolidin-3-ylcarbamate (0.80 g, 99%).

Provenance & Evidence