3-(2-Fluoropyridin-3-yl)cyclohex-2-enone → (Rac)-trans-3-(2-fluoropyridin-3-yl)cyclohexanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(2-fluoropyridin-3-yl)cyclohex-2-enone (1100 mg, 5.75 mmol) and 1,1′-bis(di-1-propylphosphino)ferrocene(1,5-cyclooctadiene)rhodium (i) tetrafluoroborate (412 mg, 0.575 mmol) in THF (40 mL) was stirred at 45° C. under an atmosphere of hydrogen gas for 5 h. The mixture was filtered through a Celite pad that was washed with THF. Concentration of the combined filtrated and washings under reduced pressure, followed by flash chromatography on silica gel (0% to 50% EtOAc in hexanes) afforded (rac)-trans-3-(2-fluoropyridin-3-yl)cyclohexanol as a colorless oil together with its cis-isomer. MS (ESI, pos. ion) m/z: 196.1 (M+1). IC50 (uM) +++++.

Provenance & Evidence