Ethanol → HCID 86742920, compound

Participants

Reaction Steps

A solution of 106.6 g (0.33 mol) of rac-(2S*)-2-[(R*)-4-(benzyloxy)-α-(nitromethyl)benzyl]cyclohexanone in 500 ml of dry tetrahydrofuran is added dropwise while stirring 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 50°. The reaction mixture is stirred at 50° overnight and it is treated, after cooling to room temperature, with 300 ml of ethanol and subsequently with 100 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 crystalline product obtained is recrystallized from methylene chloride/isopropyl ether. There is obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-(benzyloxy)benzyl]cyclohexanol in the form of colourless crystals of m.p. 160°-161°.

Provenance & Evidence