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 intermediates of this process

A method for the production of 6,7-dihydroxy steroid compounds by allylic oxidation is disclosed, wherein the method for allylic oxidation comprised the steps of: (a) providing a compound comprising a steroid carbon skeleton and two geminal allylic hydrogens as present in formula (1); (b) contacting...

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Bibliographic Details
Main Authors SHEN, YAPING, ZHOU, YUANLIN, BURGOYNE, DAVID L, PASCHALIDES, NICHOLAS D, KELLEHER, EUGENE W, JI, GUEIJUN, RAMACHANDRAN, KISHORE
Format Patent
LanguageEnglish
Published 31.08.2007
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:A method for the production of 6,7-dihydroxy steroid compounds by allylic oxidation is disclosed, wherein the method for allylic oxidation comprised the steps of: (a) providing a compound comprising a steroid carbon skeleton and two geminal allylic hydrogens as present in formula (1); (b) contacting the compound with reagents comprising an oxidizing agent (such as copper iodide and t-butyl hydroperoxide) and an amine (such as pyridine) to provide a mixture; and (c) maintaining the mixture of step (b) under oxidizing conditions to convert the compound to a product having a carbon skeleton and an a,a-unsaturated ketone moiety as present in formula (4).
Bibliography:Application Number: NZ20020546612