Water → HCID 59837378, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of LiAlH4 (1.0M in diethyl ether, 1.46 ml, 1.46 mmol) at 0° C. under an atmosphere of nitrogen was added a solution of 1-(4-{3-[(3S)-3-methoxypyrrolidin-1-yl]propoxy}phenyl)cyclohexanecarbonitrile (0.10 g, 0.29 mmol) in Et2O (2 mL) over 15 minutes maintaining the temperature at 5 to 10° C. The reaction mixture was allowed to warm up to ambient temperature for 20 minutes then refluxed for 30 minutes until complete. The reaction mixture was cooled to 0° C., water (0.5 ml) was added dropwise followed by sodium hydroxide (2.0M, 1.5 ml) and water (0.5 ml). Ethyl acetate (5 mL) was added and the mixture filtered through a short pad of celite, eluting with ethyl acetate (2×15 mL). The organic washings were dried over Na2SO4 and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, 97:3:0.3 to 90:10:1 to give the title compound as a clear oil (75 mg, 75%). 1H NMR (400 MHz, CDCl3) δ7.20 (d, 2H), 6.86 (d, 2H), 4.02 (t, 2H), 3.94-3.88 (m, 1H), 3.28 (s, 3H), 2.76-2.68 (m, 2H), 2.58-2.66 (m, 3H), 2.45-2.52 (m, 1H), 2.12-2.04 (m, 3H), 1.98 (pentet, 2H), 1.84-1.74 (m, 1H), 1.56-1.44 (m, 5H), 1.38-1.30 (m, 3H), 1.16-1.25 (m, 2H); HRMS (ESI+) 347.2693 (M+H)+.

Provenance & Evidence