反应详情

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 cis-3-(3-pyridyl)cyclohexanol (14.6 g, 75%) as colorless oil.

1. customThe catalyst was removed by filtration over Celite
2. concentrationthe filtrate was concentrated in vacuo
3. stirringstirred for 30 min at same temperature
4. extractionextracted with AcOEt
5. dry with materialThe organic layer was dried over anhyd Na2SO4
6. customfollowed by the removal of solvent
7. customThe crude product was purified by column chromatography (NH, Hexane/EtOAc=2/1)