Dichloromethane → HCID 57941429, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 150 mg, 0.56 mmol), tetrabutylammonium iodide (200 mg, 0.54 mmol) and (2-bromoethyl)benzene (500 μL, 3.7 mmol) in dimethylformamide (1.5 mL) was heated in a pressure tube in an oil-bath at 100° C. for 2 days. Dichloromethane (100 mL) was added and the solution was washed with water (4×25 mL) and aqueous sodium thiosulfate (25 mL), dried (magnesium sulfate), filtered, evaporated and purified using an ISCO 40 g column, eluting with 60-100% ethyl acetate/hexanes. Fractions homogeneous for the product were evaporated and co-evaporated successively with dichloromethane/petroleum ether and then methanol, and dried under high vacuum over the weekend at room temperature and then at 80° C. for 4 h. The residue was treated with petroleum ether to give a solid. The solvent was evaporated and the solid was dried overnight at 70° C. to give (4S,7R)-7,8,8-trimethyl-1-phenethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (30 mg, 14%) as a pale yellow solid. ES(+)-MS (M+H) 373.

Provenance & Evidence