Trifluoroacetic acid → methyl (2S,5R)-5-(4-bromophenyl)pyrrolidine-2-carboxylate

Participants

Reaction Steps

A solution of methyl (2S)-5-(4-bromophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (D76, 799 mg, 2.83 mmol) and Pt/C (50 mg) was stirred under hydrogen (1 atm) overnight. Then TFA (0.25 ml) was added and hydrogenation was continued for another 2 h. Then more Pt/C (100 mg) was added and the mixture was stirred for additional 9 h under hydrogen (1 atm). After that additional catalyst (100 mg) and TFA (0.25 ml) was added and stirring was continued for another 5 h under hydrogen atmosphere. Then additional catalyst was added (100 mg). After additional 4 h the reaction was finished and the solution was filtered over celite, evaporated and purified using a SCX cartridge to afford the title compound (641 mg, 79%). UPLC: Rt 0.47 min; MS: (ES/+) m/z: 284, 286 [MH+], C12H14BrNO2 requires 284.

Provenance & Evidence