Water → (S,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamIne

関与物質

反応手順

A solution of 4(3-trifluoromethoxyphenyl)-2-butanone (2.32 g, 10 mmol), (R)-1-(3-methoxyphenyl)ethylamine (1.51 g, 10 mmol), and titanium (IV) isopropoxide (3.55 g, 12.5 mmol) were stirred 4 hr at rt. The reaction mixture was then treated with a solution (10 ml of 1 M) of ethanolic sodium cyanoborohydride (10 mmol) and stirred 16 hr at rt. The reaction was diluted with diethyl ether (50 ml) and treated with water (0.72 ml, 40 mmol). After mixing thoroughly the solution was centrifuged and the ether layer decanted and concentrated to a oily solid. The solid was suspended in diethyl ether, filtered through 0.45 μM CR PTFE Acrodisc and concentrated to give a clear oil. Repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded the two diasteriomers, (S,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamIne, 22Z [m/z (rel. int.) 367 (M+, 3), 352 (20), 232 (4), 178 (47), 135 (100), 105 (14), 91 (10), 77 (11)] and (R,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(3-methoxyphenyl)ethylamine, 23A; m/z (rel. int.) 367 (M+, 3), 352 (19), 232 (7), 178 (43), 135 (100), 105 (19), 91 (10), 77 (11).

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