(Iodomethyl)cyclopentane → HCID 69018823, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (iodomethyl)cyclopentane (prepared according to W. L. Corbett US 20040067939; 352 mg, 1.68 mmol) and (4R,7S)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 90 mg, 0.34 mmol) was heated in an oil-bath at 100° C. for 6 days. The reaction mixture was allowed to cool and it was then diluted with dichloromethane (200 mL) and washed with water (5×30 mL), aqueous sodium thiosulfate solution (2×30 mL) and brine (30 mL). The organic extract was dried (magnesium sulfate), filtered, evaporated, and the residue purified on an Isco 40 g column, eluting with 30-100% ethyl acetate/hexanes and then held under high vacuum to give (4R,7S)-1-(cyclopentyl)methyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (4.5 mg, 4%) as a semi-solid. ES(+)-MS (M+H) 351.

Provenance & Evidence