Pyridine, hydrofluoride (1:1) → 6-(2,3-Difluorophenyl)-5-fluoro-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol

Participants

Reaction Conditions

Reaction Steps

Pyridine hydrofluoride (0.037 g, 0.38 mmol) was added dropwise to a solution of (5R,6S,9R and 5S,6R,9S)-6-(2,3-difluorophenyl)-5-fluoro-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (0.155 g, 0.345 mmol) in tetrahydrofuran (3 mL) cooled to 0° C., and the mixture was stirred for 3 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (3×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel, eluting with 55% dichloromethane in petroleum ether to give the title compound as a racemic mixture. MS: m/z=294.2 (M+1).

Provenance & Evidence