Aluminium lithium hydride → HCID 54302517, compound

Participants

Reaction Steps

A solution of 7.4 g (23.9 mmol) of rac-(2S*)-2-[4-chloro-α-(nitromethyl)benzyl]cyclooctanone in 100 ml of dry tetrahydrofuran is added dropwise at 40° while stirring to a suspension of 2.3 g (59.7 mmol) of lithium aluminium hydride in 75 ml of dry tetrahydrofuran under argon and the mixture is stirred under reflux temperature overnight. The mixture is cooled, excess lithium aluminium hydride is destroyed with 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 dissolved in ether, the ethereal phase is extracted with 1N hydrochloric acid, the acidic phase is made alkaline with conc. ammonia and extracted with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated. After crystallization from methylene chloride/isopropyl ether there is obtained rac-(2S*)-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclooctanol in the form of colourless crystals of m.p. 110°-111°.

Provenance & Evidence