Methane → (4s,7r)-2-(3,5-Dichloro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one

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Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-2-(3,5-dichloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 45; 200 mg, 0.59 mmol) and iodomethane (180 μL, 2.9 mmol) in dimethylformamide (3 mL) was heated at 95° C. for 7 h and then stirred overnight at room temperature. The solvent was evaporated, dichloromethane (50 mL) was added and the solution was washed with water (3×25 mL), saturated aqueous sodium thiosulfate (25 mL), and brine (25 mL). The solution was dried (magnesium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 20% ethyl acetate/petroleum ether, and dried under high vacuum overnight to give a pale orange solid. This was dissolved in ethanol and the solution was treated with charcoal, then filtered through Celite (washing the Celite well with ethanol) and evaporated to give a brown solid. The brown solid was dissolved in ethyl ether and the solution was cooled in a freezer for 1 h. The solid was filtered off and washed with ether to give (4S,7R)-2-(3,5-dichloro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (39 mg, 19%). ES(+)-MS (M+H) 351.

Provenance & Evidence