Methanol → HCID 66616515, compound

Participants

Reaction Steps

To a solution of N-(4-fluorophenethyl)-3-(phenethylthiomethyl)benzamide (0.3 g, 0.76 mmol) in THF (5 mL) was added borane-THF complex (1 M solution in THF, 12 mL, 12 mmol). The reaction mixture was stirred at rt for overnight. To the reaction mixture was added MeOH and 2 mL of TFA, and the resulting mixture was stirred for 3 h. The resulting mixture was concentrated and the residue was diluted with saturated NaHCO3 solution and ethyl acetate. The organic layer was separated, washed with brine, and dried over MgSO4. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography silica gel eluting with 20% ethyl acetate in hexanes, which contained 10% of 2 M ammonia in MeOH to give the desired product (0.18 g, 58%) as a colorless oil. 1H NMR (CDCl3) δ 7.32-7.14 (m, 11H), 7.01-6.95 (m, 2H), 3.84 (s, 2H), 3.72 (s, 2H), 2.91-2.80 (m, 6H), 2.73-2.64 (m, 2H). MS (ESI): 380.1 (M+H)+.

Provenance & Evidence