Benzylideneacetone → HCID 66895711, compound

Participants

Reaction Steps

In a similar fashion, an equal molar amount of (R)-1-(3-methoxyphenyl)ethylamine, trans-4-phenyl-3-butene-2-one and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of 1 M, 5 mmol). Work-up and chromatography afforded (R,R)-N-(2-methyl-4-phenybut-3-enyl)-1-(3-methoxyphenyl)ethylamine, 25H, as an oil; m/z (rel. int.) 283 (M+, 4), 268 (13), 178 (40), 135 (100), 105 (15), 91 (47), 77 (13) and (S,R)-N-(2-methyl-4-phenybut-3-enyl)-1-(3-methoxyphenyl)ethylamine, 25I, as an oil; m/z (rel. int.) 283 (M+, 4), 268 (13), 178 (40), 135 (100), 105 (15), 91 (47), 77 (13).

Provenance & Evidence