Process improvements in steroid chemistry

US6982329B2 · kind B2 · utility

Assignee

• INFLAZYME PHARMACEUTICALS LTD. · CA

Inventors

• David L. Burgoyne · Delta, CA
• Gueijun Ji · Richmond, US
• Eugene Kelleher · Somerville, US
• Nicholas Paschalides · Marlborough, US
• Kishore Ramachandran · Burlington, US
• Yaping Shen · Port Coquitlam, CA
• Yuanlin Zhou · Richmond, CA

Key dates

• Filing date: Dec 22, 2003
• Grant date: Jan 3, 2006
• Expiry date: Dec 22, 2023

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding α,β-unsaturated ketone using copper iodide and t-butyl hydroperoxide. A steroid compound containing the α,β-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.