Process for the production of 6,7-dihydroxy steroid compounds by allylic oxidation of steroid-5-ene compounds to steroid-5-ene-7-one compounds followed by hydroboration and oxidation and intermediates of this process

Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the alpha,beta-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol usi...

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Bibliographic Details
Main Authors GUEIJUN JI, YUANLIN ZHOU, DAVID L. BURGOYNE, EUGENE W. KELLEHER, YAPING SHEN, KISHORE RAMACHANDRAN, NICHOLAS D. PASCHALIDES
Format Patent
LanguageEnglish
Published 24.11.2004
Edition7
Subjects
APPARATUS THEREFOR
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
STEROIDS
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Summary:Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding alpha,beta-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the alpha,beta-unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.
Bibliography:Application Number: ZA20030008967