Benzylamine → 5-Benzylamino-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

Participants

Reaction Steps

To a solution of 2-(4-Trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione (0.5 g, 1.6 mmol) and benzylamine (0.34 g, 3.2 mmol) in dichloromethane (10 mL) were added NaBH(AcO)3 (1.0 g, 4.7 mmol). The mixture was stirred for 6 h at ambient temperature. The mixture was extracted with dichloromethane (2×15 mL), washed with brine (30 mL), dried over anhydrous Na2SO4. The solvent was removed, and the crude product was purified by silica column (MeOH/dichloromethane=1/30) to yield the title compound (0.4 g, 63%). 1H NMR (300 MHz, CDCl3): δ 7.67-7.63 (m, 2H), 7.32-7.07 (m, 7H), 4.08 (t, 1H, J=9.3 Hz), 3.76-3.56 (m, 3H), 3.34-3.31 (m, 1H), 3.16-3.09 (m, 1H), 2.88-2.83 (m, 1H), 2.21-2.02 (m, 3H), 1.65-1.58 (m, 1H).

Provenance & Evidence