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: SHEN, YAPING, PASCHALIDES, NICHOLAS, D, BURGOYNE, DAVID, L, ZHOU, YUANLIN, KELLEHER, EUGENE W, JI, GUEIJUN, RAMACHANDRAN, KISHORE
• Format: Patent
• Language: English; French; German
• Published: 07.04.2004
• 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.