反应详情

To a stirred solution of 17β-hydroxy-4,4-dimethylandrost-5-en-3-one (408 mg) in THF (12 ml) at −15° C., under N2, was added 1M BH3.THF complex in THF (6.44 ml). The mixture was then stirred at RT overnight. H2O (5 ml) was cautiously added dropwise followed by NaBO3.4H2O (330 mg). After stirring at RT overnight, the mixture was filtered. The solid was washed with THF and then discarded. The liquid phases were separated and the aqueous layer was saturated with NaCl and extracted with THF (3×200 ml). The combined organic extracts were dried over NaCl and Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, DCM/MeOH 97/3) to give 4,4-dimethylandrostan-3β,6α,17β-triol (137 mg, 32%).

1. stirringAfter stirring at RT overnight
2. filtrationthe mixture was filtered
3. washThe solid was washed with THF
4. customThe liquid phases were separated
5. extractionextracted with THF (3×200 ml)
6. dry with materialThe combined organic extracts were dried over NaCl and Na2SO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe crude product was purified by flash chromatography (SiO2, DCM/MeOH 97/3)