Methyl iodide → HCID 57941434, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-2-(4-hydroxy-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 41; 1.60 g, 5.6 mmol) and iodomethane (1.1 mL, 17.7 mmol) in dimethylformamide (50 mL) was heated in a sealed tube at about 100° C. for 2.5 h. The reaction mixture was allowed to cool to room temperature. The tube was carefully opened, and the contents were allowed to stand at room temperature over a weekend. The solvent was evaporated and dichloromethane (250 mL) was added. The solution was washed with water (100 mL), saturated sodium thiosulfate (100 mL), water (100 mL), and brine (100 mL). The organic layer was dried (magnesium sulfate), filtered, and evaporated. The residue was triturated with ethyl acetate and the solid was filtered off and washed with 20% ethyl acetate/hexanes and then hexanes, and then purified using a Biotage 40M system, eluting with 3-5% methanol/dichloromethane to give (4S,7R)-2-(4-Hydroxy-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (1.26 g, 75%) as a light yellow solid. APCI(+)-MS (M+H) 299.

Provenance & Evidence