Water → 1-(4-{[2-(3-Trifluoromethyl-phenyl)-ethylamino]-methyl}-phenyl)-cyclopropanecarbonitrile

Participants

Reaction Steps

46 mg (1.23 mmol) of sodium borohydride were added to 135 mg (0.31 mg) of N-[4-(1-cyano-cyclopropyl)-benzyl]-2,2,2-trifluoro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-acetamide dissolved in 3.1 ml ethanol under nitrogen. The reaction mixture was stirred at rt for 3 h. Under ice bath cooling water was added and the reaction mixture was extracted twice with EtOAc. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (25 g silica gel; methylene chloride/methanol=19:1) to yield 81 mg (77%) of 1-(4-{[2-(3-trifluoromethyl-phenyl)-ethylamino]-methyl}-phenyl)-cyclopropanecarbonitrile as a colorless oil. 1HNMR (DMSO-d6, 300 MHz): δ 7.61-7.47 (m, 4H), 7.30 (d, 2H), 7.24 (d, 2H), 3.69 (s, 2H), 2.81 (t, 2H), 2.73 (t, 2H), 1.72 (m, 2H), 1.44 (m, 2H).

Provenance & Evidence