(2S)-2-[(1R)-1-(4-chlorophenyl)-2-nitroethyl]cyclohexan-1-one → HCID 57108580, compound

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Reaction Steps

A solution of 4.55 g (16.1 mmol) of (-)-(2S)-[(R)-4-chloro-α-(nitromethyl)benzyl]cyclohexanone [prepared according to Helv. Chim. Acta 65, 1637 (1982)] in 80 ml of dry tetrahydrofuran is added dropwise at room temperature while stirring to a suspension of 1.5 g (40.4 mmol) of lithium aluminium hydride in 50 ml of dry tetrahydrofuran under argon. The reaction mixture is stirred at room temperature overnight, treated with 20 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 dissolved in ether, the ethereal phase is extracted with 1N hydrochlorid acid, the acidic phase is made alkaline with 3N sodium hydroxide solution and extracted with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated. There is obtained (+)-(1S)-cis-2-[(R)-α-(aminomethyl)-4-chlorobenzyl]cyclohexanol in the form of a yellow oil ([α]D20 =+14.7°, c=0.6 in chloroform), which is processed as such.

Provenance & Evidence