Iodoethane → HCID 69018277, compound

Participants

Reaction Steps

Iodoethane (0.12 mL, 1.5 mmol) was added to (4S,7R)-7,8,8-trimethyl-2-p-tolyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 9; 400 mg, 1.4 mmol) and potassium carbonate (400 mg, 2.8 mmol) in dimethylformamide (5 mL). The mixture was heated at 60 degrees under argon overnight. The reaction mixture was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified using an Analogix Intelliflash 280 system (Analogix, Inc., Burlington, Wis.) with an RS-12 column, eluting with 0-75% ethyl acetate/hexanes to give (4S,7R)-1-ethyl-7,8,8-trimethyl-2-p-tolyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (30 mg, 7%) as a white solid and (4S,7R)-3-ethoxy-7,8,8-trimethyl-2-p-tolyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (266 mg, 60%) as a light yellow solid. ES(+)-MS (M+H) 311.

Provenance & Evidence