Potassium Carbonate → HCID 86742918, compound

Participants

Reaction Steps

A solution of 41.6 g (0.15 mol) of rac-(2S*)-2-[(R*)-3-methoxy-α-(nitromethyl)benzyl]cyclohexanone in 400 ml of dry tetrahydrofuran is added dropwise to a suspension of 14.2 g (0.38 mol) of lithium aluminum hydride in 400 ml of dry tetrahydrofuran under argon. The reaction mixture is then heated to boiling under reflux for 4 hours, treated, after cooling, firstly with 50 ml of ethanol, and subsequently with tetrahydrofuran/water (1:1), treated with 80 g of potassium carbonate and stirred for 30 minutes. The separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The residue is treated with 3N hydrochloric acid and extracted twice with 250 ml of ether each time. The aqueous phase is made alkaline with 3N sodium hydroxide solution and extracted twice with 500 ml of ether each time. The organic phase is washed twice with 50 ml of sodium chloride solution each time, dried over magnesium sulphate and evaporated. The crude product obtained as a yellowish oil is converted into the oxalate which is recrystallized from acetone. The rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-3-methoxybenzyl]cyclohexanol oxalate (2:1) obtained melts at 210°212°.

Provenance & Evidence