Trifluoroacetic acid → (R)-Phenyl[(2R,5S)-5-(4-{[4-(pyridin-2-ylmethyl)piperazin-1-yl]carbonyl}benzyl)pyrrolidin-2-yl]methanol

Participants

Reaction Steps

A solution of 0.038 g (0.067 mmol) of the title compound from Step A above in 1 mL dichloromethane and 1 mL trifluoroacetic acid was stirred at ambient temperature for 1 h. All volatiles were removed in vacuo and the crude light brown residue was purified directly by reverse-phase HPLC to afford the title compound (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). 1H-NMR (500 MHz, CD4O) δ 8.70 (d, J=4.9 Hz, 1H), 7.99-7.98 (m, 1H), 7.59 (d, J=7.8 Hz, 1H), 7.53-7.34 (m, 10H), 4.76 (d, J=8.8 Hz, 1H), 4.51 (s, 2H), 4.10-3.81 (m, 6H), 3.42-3.39 (m, 4H), 3.33-3.08 (m, 2H), 2.10-2.00 (m, 1H), 1.86-1.75 (m, 3H). LC/MS: m/z (ES) 471.3 (MH)+, 493.3 (MNa)+.

Provenance & Evidence