反应详情

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androst-5-ene (1.0 g), were added hexane (15 ml), N-bromosuccinimide (336.4 mg) and then 2,2′-azobis isobutyronitrile (77.6 mg), followed by reaction under reflux for 30 min. After cooling with ice, the mixture was filtered to remove insoluble material and the filtrate was evaporated under reduced pressure to remove the solvent. To the resulting residue, were added toluene (10 ml) and γ-collidine (534.4 mg), followed by reflux for 2 hours. The mixture was filtered to remove insoluble material and the filtrate was diluted with hexane. The organic layer was washed with IM hydrochloric acid, a saturated aqueous sodium bicarbonate solution and then saturated brine and evaporated to remove the solvent under reduced pressure. The resulting residue was purified by column chromatography (hexane:ethyl acetate 40:1), dissolved in dichloromethane (20 ml) and subjected to reaction for 1 hour by adding 4-phenyl-1,2,4-triazoline-3,5-dione. The reaction mixture was evaporated to remove the solvent under reduced pressure and the resulting residue was purified by column chromatography (hexane:ethyl acetate=7:1) to give the titled compound (0.45 g).

1. temperatureunder reflux for 30 min
2. temperatureAfter cooling with ice
3. filtrationthe mixture was filtered
4. customto remove insoluble material
5. customthe filtrate was evaporated under reduced pressure
6. customto remove the solvent
7. additionTo the resulting residue, were added toluene (10 ml) and γ-collidine (534.4 mg)
8. temperatureby reflux for 2 hours
9. filtrationThe mixture was filtered
10. customto remove insoluble material
11. additionthe filtrate was diluted with hexane
12. washThe organic layer was washed with IM hydrochloric acid
13. customa saturated aqueous sodium bicarbonate solution and then saturated brine and evaporated
14. customto remove the solvent under reduced pressure
15. customThe resulting residue was purified by column chromatography (hexane:ethyl acetate 40:1)
16. dissolutiondissolved in dichloromethane (20 ml)
17. customsubjected to reaction for 1 hour
18. customThe reaction mixture was evaporated
19. customto remove the solvent under reduced pressure
20. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=7:1)