Bromomethylcyclopropane → HCID 57941385, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-2-(2-chloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 10; 154 mg, 0.51 mmol), tetrabutylammonium iodide (752 mg, 2.0 mmol), and (bromomethyl)cyclopropane (Lancaster; 195 μL, 2.0 mmol) in dimethylformamide (4.3 mL) was heated in an oil-bath at 100° C. for 16 h. The solvent was evaporated and the residue was partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane (2×100 mL) and the combined organic layers were washed with water (5×100 mL) and aqueous sodium thiosulfate (100 mL). The solvent was evaporated and the residue was purified using an ISCO 120 g column, eluting with 65-100% ethyl acetate/hexanes to give (4S,7R)-2-(2-chloro-phenyl)-1-cyclopropylmethyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (60 mg, 33%) as a yellow gum. ES(+)-MS (M+H) 357.

Provenance & Evidence