HCID 66811108, compound → HCID 57911421, compound

Participants

Reaction Steps

Racemic trans-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol and cis-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol. In a 500 mL round-bottomed flask was (E)-6-(2,3-difluorophenyl)-8,9-dihydro-7H-cyclohepta[b]pyridin-9-ol (660 mg, 2.415 mmol) in MeOH (20 mL) to give a colorless solution. Pd/C (257 mg, 0.242 mmol) was added, and the mixture was stirred under hydrogen balloon for 4 h. LCMS showed complete conversion. Filtered and concentrated to a colorless oil. Purification by FCC up to 80% EtOAc/hexane afforded two products: trans-alcohol (104.3 mg, 16%), and cis-alcohol (492.8 mg, 74%), both as white solids. Analytical data of both alcohols matched that of previously described.

Provenance & Evidence