Dimethyl Sulfate → HCID 57941349, compound

Participants

Reaction Steps

Dimethyl sulfate (0.6 mL, 6.3 mmol) was added to a mixture of (4S,7R)-2-(3-iodo-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 18; 1.62 g, 4.1 mmol) in methanol (10 mL) and 1 M NaOH (20 mL). The mixture was stirred at room temperature overnight and then further portions of dimethyl sulfate (0.6 mL, 6.3 mmol) were added immediately, after 2 h, and after 5 h. The mixture was stirred at room temperature over the weekend, and it was then diluted with water and extracted with ethyl acetate (2×125 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried (magnesium sulfate), filtered, evaporated, and purified using an Analogix Intelliflash 280 system (Analogix, Inc., Burlington, Wis.) with an RS-90 column, eluting with 0-100% ethyl acetate/hexanes to give (4S,7R)-2-(3-iodo-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (620 mg, 38%), as a white solid, (4S,7R)-2-(3-iodo-phenyl)-3-methoxy-7,8,8-trimethyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (606 mg, 37%) as a yellow solid and unreacted starting material (140 mg, 9%). ES(+)-MS (M+H) 409.

Provenance & Evidence