Ethanol → HCID 54216346, compound

Participants

Reaction Steps

A solution of 112 g (0.4 mol) of rac-(2S*)-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanone in 1 l of dry tetrahydrofuran is added dropwise under argon to a suspension of 39 g (1.03 mol) of lithium aluminium hydride in 1 l of dry tetrahydrofuran so that the temperature does not exceed 50°, whereupon the reaction mixture is stirred at 50° overnight. After cooling to room temperature the reaction mixture is treated with 50 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 oil obtained is dissolved in 1 l of ether and the solution is left to stand at room temperature overnight. The separated colourless crystals are filtered off under suction, there being obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclohexanol of m.p. 108°-110°. The rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclohexanol hydrochloride prepared from the base in the usual manner is recrystallized from ethanol/ether and melts at 259°-260° (decomposition).

Provenance & Evidence