Sodium borohydride → HCID 21978391, compound

Participants

Reaction Steps

To a solution of 2-{1-[2-(2,4-difluorophenyl)ethyl]azetidin-3-yl}-1-phenylethanone (Example 20, 41 mg, 0.117 mmol) in methanol (1 mL) under nitrogen was added sodium borohydride (8.8 mg, 0.23 mmol). The reaction was stirred at room temperature overnight. More sodium borohydride (5 mg, 0.13 mmol) was added and the reaction stirred for 30 minutes. More sodium borohydride (8.8 mg, 0.23 mmol) was added and the reaction stirred for 15 minutes. More sodium borohydride (5 mg, 0.13 mmol) was added and the reaction stirred overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica, eluting with 10% methanol/dichloromethane, to give the title compound. 1H NMR (360 MHz, CDCl3) δ 7.35–7.29 (5H, m), 7.22–7.16 (1H, m), 6.81–6.73 (2H, m), 4.71 (1H, dd, J=5.3, 7.6 Hz), 3.63 (1H, s), 3.53 (1H, s), 3.11 (1H, s), 2.98 (1H, s), 2.77 (5H, s), 2.07–1.92 (2H, m); m/z (ES+) 318 (M+H)+.

Provenance & Evidence