Ethanol → HCID 86742919, compound

Participants

Reaction Steps

A solution of 106.6 g (0.3 mol) of rac-(2S*)-2-[(R*)-3-(benzyloxy)-α-(nitromethyl)benzyl]cyclohexanone in 500 ml of dry tetrahydrofuran is added drowpise while stirring within about 3 hours to a suspension of 28.6 g (0.75 mol) of lithium aluminium hydride in 500 ml of dry tetrahydrofuran under argon so that the temperature does not exceed 55°. The reaction mixture is stirred at 50° overnight, treated, after cooling, with 40 ml of ethanol and subsequently with 200 ml of tetrahydrofuran/water (1:1), the separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The residue is crystallized from methylene chloride/isopropyl ether, there being obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-3-(benzyloxy)benzyl]cyclohexanol in the form of colourless crystals of m.p. 139°-141°.

Provenance & Evidence