1-Iodo-3-methylbutane → (4s,7r)-2-(2-Chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1-(3-methyl-butyl)-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-(2-chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 21; 200 mg, 0.62 mmol) and 1-iodo-3-methylbutane (410 μL, 3.1 mmol) in dimethylformamide (4 mL) was heated at 100° C. overnight and then stirred at room temperature over the weekend. The solvent was evaporated and dichloromethane (50 mL) was added. The solution was washed with water (2×20 mL), saturated aqueous sodium thiosulfate (20 mL), and brine (20 mL), dried (magnesium sulfate), filtered, concentrated, purified by chromatography, eluting with 65% ethyl acetate/petroleum ether, and dried under high vacuum over the weekend to give (4S,7R)-2-(2-chloro-4-fluoro-phenyl)-7,8,8-trimethyl-1-(3-methyl-butyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (91 mg, 38%) as an off-white solid. APCI(+)-MS (M+H) 391.

Provenance & Evidence