Dimethyl Sulfate → HCID 69021044, compound

Participants

Reaction Steps

(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) was dissolved in 1 M NaOH (5 mL) and dimethyl sulfate (0.14 mL, 1.46 mmol) was added. The mixture was stirred at room temperature overnight and then 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 0-100% ethyl acetate/hexanes to give (4S,7R)-1,7,8,8-tetramethyl-2-p-tolyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (82 mg, 20%) as an off-white solid and (4S,7R)-3-methoxy-7,8,8-trimethyl-2-p-tolyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (134 mg, 32%) as a yellow solid. ES(+)-MS (M+H) 297.

Provenance & Evidence