Water → HCID 57941517, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of a (4S,7R)-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 12; 1.06 g, 3.7 mmol) and iodomethane (450 μL, 7.2 mmol) in N,N-dimethylformamide (20 mL) in a sealed tube was heated to 98° C. and stirred for 5 h. The reaction mixture was allowed to cool and water (20 mL) and saturated sodium bicarbonate solution (200 mL) were added. The solution was extracted with ethyl acetate (200 mL), and the organic layer was washed with brine (200 mL), dried (sodium sulfate), filtered, and evaporated. The residue was triturated with hexanes (4×5 mL) and the solid was recrystallized twice from ethyl acetate/hexanes to give (4S,7R)-2-(2-fluoro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (451 mg, 41%) as white needles. ES(+)-MS (M+H) 301.

Provenance & Evidence