Dimethyl Sulfoxide → HCID 57911403, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (0.91 mL, 11 mmol) in dichloromethane (15 mL) at −65° C. was added DMSO (0.94 mL, 13 mmol), and the mixture was stirred for 30 min. A solution of racemic trans 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol (prepared according to the procedures described by Leahy, D. K et al Org. Lett. 2012, 14, 4938-4941, 365 mg, 1.33 mmol) in dichloromethane (3 mL) was added drop wise and the resulting solution was stirred at −65° C. for 30 min. Triethylamine (2.55 mL, 18.6 mmol) was added and the reaction mixture was gradually warmed to 23° C. over a period of 4 h, and then partitioned between water and dichloromethane. The organic layer was washed with water (3×), brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 35% ethyl acetate in petroleum ether to give the title compound as a racemic mixture. MS: m/z=274.2 (M+1).

Provenance & Evidence