Methane → HCID 57941478, 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 (207 mg, 0.56 mmol) and 2-bromoethyl methyl ether (540 μL, 5.75 mmol) in dimethylformamide (3 mL) was heated in an oil-bath at 100° C. for 17 h. An additional portion of 2-bromoethyl methyl ether (540 μL, 5.75 mmol) was added and the mixture was heated at 100° C. for 3 days. Dichloromethane (75 mL) and water (25 mL) were added, and the aqueous layer was back-extracted with dichloromethane (2×30 mL). The combined organic layers were washed with water (4×20 mL), aqueous sodium thiosulfate (20 mL), and brine (30 mL). The solution was dried (magnesium sulfate), filtered, evaporated and the residue was purified using an ISCO 40 g column, eluting with 20-100% ethyl acetate/hexanes to give an orange oil. This was treated with charcoal in methanol and the mixture was filtered through Celite. The solvent was evaporated to give (4S,7R)-1-(2-methoxy-ethyl)-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (10.3 mg, 6%) as an orange oil. The purity of the sample was assessed at 88% by 1H NMR. ES(+)-MS (M+H) 327.

Provenance & Evidence