Isoxazole, 4-(chloromethyl)-3,5-dimethyl- → HCID 57941432, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 4-chloromethyl-3,5-dimethyl-isoxazole (60 μL, 0.48 mmol) in N,N-dimethylformamide (5 mL) was heated at 100° C. overnight. A further portion of and 4-chloromethyl-3,5-dimethyl-isoxazole (30 μL, 0.24 mmol) was added and the solution was heated at 100° C. for 2 h. The reaction mixture was evaporated and the residue was diluted with water and extracted with chloroform. The chloroform layer was washed with water, dried (magnesium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 3% methanol/dichloromethane to give (4S,7R)-2-(3,5-Dimethyl-isoxazol-4-ylmethyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (62 mg, 41%) as an off-white solid. ES(+)-MS (M+H) 316.

Provenance & Evidence