Dimethyl Sulfate → HCID 57941367, compound

Participants

Reaction Steps

Dimethyl sulfate (84 μL, 0.92 mmol) was added to a solution of (4S,7R)-2-(4-chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 11; 252 mg, 0.83 mmol) in 1 M NaOH (3 mL) and the resulting solution was stirred at room temperature overnight. The aqueous supernatant was decanted away from the red gum, and the gum was dissolved in ethyl acetate. This solution was washed with water, dried (sodium sulfate), filtered, evaporated, and purified by chromatography using a Waters Sep-Pak® column, eluting with 20% ethyl acetate/hexanes to elute 2-(4-chloro-phenyl)-3-methoxy-7,8,8-trimethyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole, and then a step gradient of 50% ethyl acetate/hexanes, 66% ethyl acetate/hexanes, and finally 4% methanol/ethyl acetate to give (4S,7R)-2-(4-chloro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (18 mg, 7%). ES(+)-MS (M+H) 317.

Provenance & Evidence