Sodium borohydride → trans-3-(3-Pyridyl)cyclohexanol

Participants

Reaction Steps

A mixture of 3-(3-pyridyl)-2-cyclohexen-1-one (19.1 g, 110 mmol) and 10% Pd/C (1.91 g) in EtOH (300 mL) was stirred under hydrogen atmosphere for 16 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. To a solution of crude product in MeOH (360 ml) was added portionwise NaBH4 (2.08 g. 55.0 mmol) at 3° C., and stirred for 30 min at same temperature. The reaction mixture was poured into ice-water and then extracted with AcOEt. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (NH, Hexane/EtOAc=2/1) to yield trans-3-(3-pyridyl)cyclohexanol (4.19 g, 21%) as colorless powder.

Provenance & Evidence