Methane → HCID 69020926, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of cyclohexylmethyl bromide (2.1 mL, 15 mmol), (4R,7S)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 395 mg, 1.47 mmol) and tetra-n-butylammonium iodide (400 mg, 1.08 mmol) in N,N-dimethylformamide (4 mL) was heated in an oil-bath at 100° C. for 64 h. Additional quantities of in N,N-dimethylformamide (2 mL), cyclohexylmethyl bromide (2.1 mL, 15 mmol), and tetra-n-butylammonium iodide (400 mg, 1.08 mmol) were added and the mixture was heated at 135° C. for 20 h. An additional quantity of cyclohexylmethyl bromide (2.1 mL, 15 mmol) was added and the mixture was heated at 135° C. for 6 days. The reaction mixture to cooled to room temperature and then diluted with dichloromethane (150 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 15-100% ethyl acetate/hexanes and then held under high vacuum to give an orange gum. This was treated with charcoal in methanol in a warm water bath, and the resulting mixture was filtered, evaporated and held under high vacuum to give (4R,7S)-1-(cyclohexyl)methyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (22 mg, 4%) as a yellow gum. ES(+)-MS (M+H) 365.

Provenance & Evidence