Water → HCID 57941506, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-2-(2,6-dichloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 15; 1.2 g, 3.6 mmol) and iodomethane (0.45 mL, 8.0 mmol) in N,N-dimethylformamide (20 mL) was heated to 80° C. and stirred for 4.5 h. The reaction mixture was allowed to cool and water (200 mL) was added. A solid precipitated. Water (100 mL) was added, and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated sodium bicarbonate and brine, dried (sodium sulfate), filtered, concentrated and purified by chromatography, eluting with 5-80% ethyl acetate/dichloromethane. Fractions containing the product were combined, evaporated, and recrystallized from ethyl acetate/hexanes to give (4S,7R)-2-(2,6-dichloro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (220 mg 18%) as a light tan solid. ES(+)-MS (M+H) 351

Provenance & Evidence