Sodium borohydride → HCID 67606120, compound

Participants

Reaction Steps

Sodium borohydride (7.7 g) was added portionwise to a stirred solution of 3-methoxy-1-(phenylmethyl)-4-piperidinone (44.8 g) in ethanol (610 ml). Upon completion, the whole was cooled to room temperature and stirring was continued for 3 hours at room temperature. The reaction mixture was concentrated to a volume of about 150 ml. Water (300 ml) was added to the concentrate and all traces of ethanol were evaporated. After cooling, the mixture was extracted with diethylether. The extract was washed with water, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel (eluent: CHCl3 /CH3OH 96/4). The pure fractions were collected and the eluent was evaporated. The residue was separated by column-chromatography over silica gel (eluent: hexane/CHCl3 /(CH3OH/NH3) 50/50/1). The first fraction was collected and the eluent evaporated, yielding 11.5 g (25.5%) of trans-3-methoxy-1-(phenylmethyl)-4-piperidinol (intermediate 1). The second fraction was collected and the eluent evaporated, yielding 7.7 g (17.1%) of cis-3-methoxy-1-(phenylmethyl)-4-piperidinol (intermediate 2).

Provenance & Evidence