Dimethyl Sulfate → HCID 69018306, compound

Participants

Reaction Steps

Dimethyl sulfate (66 μL, 0.7 mmol) was added to (4R,7S)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 7; 185 mg, 0.7 mmol) in 1 M NaOH (5 mL). The mixture was vortexed and then heated with a heat gun for 30 sec., then shaken for 10 min, and extracted twice with dichloromethane. TLC indicated that the sodium hydroxide solution still contained starting material so a further quantity of dimethyl sulfate (150 μL, 1.6 mmol) was added and the mixture was vortexed, heated with a heat gun for 30 sec and then heated for 90 min at 100 degrees. The mixture was extracted with dichloromethane and the combined dichloromethane extracts were evaporated and purified by column chromatography, eluting initially with 50% ethyl acetate/hexanes and later with 12.5% methanol/ethyl acetate to give (4R,7S)-3-methoxy-7,8,8-trimethyl-2-phenyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (70 mg, 35%) as a yellow solid, and (4R,7S)-1,7,8,8-tetramethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (33 mg, 17%) as a white solid. APCI-MS (M+H) 283.

Provenance & Evidence