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

• Main Authors: GUEIJUN JI, YUANLIN ZHOU, DAVID L. BURGOYNE, EUGENE W. KELLEHER, YAPING SHEN, KISHORE RAMACHANDRAN, NICHOLAS D. PASCHALIDES
• Format: Patent
• Language: English
• Published: 24.11.2004
• Edition: 7
• 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

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.