反应详情

温度

95 °C

A mixture of (4S,7R)-2-(3,5-dichloro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 45; 400 mg, 1.2 mmol) and iodoethane (480 μL, 5.95 mmol) in dimethylformamide (5 mL) was heated at 95° C. for 7 h and then a further portion of iodoethane (480 μL, 5.95 mmol) was added. The solution was heated at 95° C. overnight. The solvent was evaporated, dichloromethane (100 mL) was added and the solution was washed with water (3×50 mL), saturated aqueous sodium thiosulfate (50 mL), and brine (50 mL). The solution was dried (magnesium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 20% ethyl acetate/petroleum ether, and dried under high vacuum over the weekend to give a pale orange solid. The solid was stirred in a small amount of ether, and the insoluble material was filtered off and dried under high vacuum overnight to give (4S,7R)-2-(3,5-dichloro-phenyl)-1-ethyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (30 mg, 7%). ES(+)-MS (M+H) 351.

1. temperatureThe solution was heated at 95° C. overnight
2. customThe solvent was evaporated
3. additiondichloromethane (100 mL) was added
4. washthe solution was washed with water (3×50 mL), saturated aqueous sodium thiosulfate (50 mL), and brine (50 mL)
5. dry with materialThe solution was dried (magnesium sulfate)
6. filtrationfiltered
7. customevaporated
8. custompurified by column chromatography
9. washeluting with 20% ethyl acetate/petroleum ether
10. customdried under high vacuum over the weekend
11. customto give a pale orange solid
12. filtrationthe insoluble material was filtered off
13. customdried under high vacuum overnight