反应详情

温度

100 °C

A mixture of (bromomethyl)cyclopropane (263 μL, 2.75 mmol), (4R,7S)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 184 mg, 0.69 mmol) and tetra-n-butylammonium iodide (1.02 g, 2.75 mmol) in N,N-dimethylformamide (4.3 mL) was heated in an oil-bath at 100° C. for 16 h. The solvent was evaporated and dichloromethane (100 mL) and water were added. The aqueous layer was extracted with dichloromethane (2×100 mL) and the combined organic layers were washed with water (5×100 mL) and then with sodium thiosulfate solution (100 mL). The solvent was evaporated and the residue purified on an Isco 120 g column, eluting with 33-100% ethyl acetate/hexanes to give (4R,7S)-1-(cyclopropyl)methyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (108 mg, 49%) as an off-white/tan oil. APCI-MS (M+H) 323.

1. customThe solvent was evaporated
2. additiondichloromethane (100 mL) and water were added
3. extractionThe aqueous layer was extracted with dichloromethane (2×100 mL)
4. washthe combined organic layers were washed with water (5×100 mL)
5. customThe solvent was evaporated
6. customthe residue purified on an Isco 120 g column
7. washeluting with 33-100% ethyl acetate/hexanes