Triethylamine → 6-(2,3-Difluorophenyl)-5-fluoro-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

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Reaction Conditions

Reaction Steps

Deoxo-Fluor® (0.148 g, 0.670 mmol) was added dropwise to a solution of (5S,6S,9R and 5R,6R,9S)-6-(2,3-difluorophenyl)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol (prepared according to the procedures described by Leahy, D. K et al Org. Lett. 2012, 14, 4938-4941, 0.30 g, 0.67 mmol) and triethylamine (0.093 mL, 0.67 mmol) in 1,2-dichloroethane (2 mL) at 0° C. The resulting mixture was gradually warmed to 23° C. and stirred for 2 h, then partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane (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 35% dichloromethane in petroleum ether to give the title compound as a racemic mixture. MS: m/z=450.2 (M+1).

Provenance & Evidence