Process for making epoxide intermediates

US6066751A · kind A · utility

Assignee

• The Procter & Gamble Company · US

Inventors

• John August Wos · Cincinnati, US
• Jack Snyder Amburgey, Jr. · Loveland, US
• Mitchell A. deLong · Chapel Hill, US
• Yili Wang · Mason, US
• Haiyan George Dai · Drexel Hill, US
• Biswanath De · Mason, US

Key dates

• Filing date: Sep 4, 1998
• Grant date: May 23, 2000
• Expiry date: Sep 4, 2018

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C405/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

It has been surprisingly discovered that the disadvantages of the lengthy literature procedures to synthesize 13,14-dihydro prostaglandin A, E, and F derivatives can be overcome using a novel Methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2 tetramethyl-1-silapropoxy)cyclopentyl) heptanoate intermediate, which can be synthesized from commercially available Methyl 7-[3-(R)-hydroxy-5-oxo-1-cyclopent-1-yl] heptanoate. This novel intermediate can be coupled with oxygen, carbon, sulfur, and nitrogen nucleophiles, in the presence of a base or a Lewis acid, in a ring-opening process to provide 13,14-dihydro prostaglandin A, E, and F derivatives.