(S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate → Methyl (5S)-5-{4-[(phenylmethyl)oxy]phenyl}-L-prolinate

Participants

Reaction Steps

To a solution of methyl (2S)-5-{4-[(phenylmethyl)oxy]phenyl}-3,4-dihydro-2H-pyrrole-2-carboxylate (D7, 13.7 g, 32.4 mmol) in MeOH (200 ml) was added PtO2 (240 mg) and the mixture was stirred under hydrogen atmosphere (2 atm) for 6 hours. Then the catalyst was filtered off and the solvent removed under reduced pressure to give a red oil which was dissolved in ethyl acetate and washed with NaHCO3 solution. The resulting crude material was purified by chromatography on silica gel eluting with cyclohexane/ethyl acetate (9:1 to 8:2) to afford the title compounds:

Provenance & Evidence