Ethanol → (1RS,2RS,4SR)-3-[4-(2-cyclopentyl-ethyl)-2-dimethylaminomethyl-1-hydroxy-cyclohexyl]-phenol hydrochloride

Participants

Reaction Steps

The reaction was conducted in a nitrogen atmosphere with the exclusion of moisture. 1.44 g (4 mmole) of the base of compound (52) were dissolved in 15 ml toluene. 25 ml of 20% diisobutylaluminium hydride in toluene (35 mmole) were added drop-wise with stirring. The mixture was subsequently boiled for 6.5 hours under reflux and was cooled. 5 ml ethanol, followed by 5 ml of 1:1 ethanol/water and 35 ml toluene, were added drop-wise at a temperature between 0° C. and 10° C. After stirring for one hour, the salts obtained were filtered off by suction and the solvent was removed by distillation. The oil obtained was then taken up in ethyl acetate. After adding trimethylchlorosilane/water, compound (57) was obtained in a yield of 0.35 g (23% theoretical).

Provenance & Evidence