Method of preparing enantiomerically-pure 3-methyl-5-(1-alkyl-2(S)-pyrrolidinyl) isoxazoles

US5424444A · kind A · utility

Assignee

• Abbott Laboratories · US

Inventors

• Nan-Horng Lin · Mundelein, US
• Yun He · Zion, US
• Richard L. Elliott · East Lyme, US
• Mukund S. Chorghade · Natick, US
• Thomas K. J. Esch · Hohentengen, DE
• Dieter O. Beer · Waldshut-Tiengen, DE
• Christian C. Witzig · Zürich, CH
• Thomas Herzig · Leonberg, DE
• Steven J. Wittenberger · Mundelein, US
• William H. Bunnelle · Mundelein, US
• Bikshandar A. Narayanan · Mundelein, US
• Pulla Singam · Waukegan, US
• Alla V. Rama Rao · Hyderabad, IN

Key dates

• Filing date: Apr 28, 1994
• Grant date: Jun 13, 1995
• Expiry date: Apr 28, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D413/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A novel process for preparing enantiomerically-pure 3-methyl-5-(1-(C.sub.1 -C.sub.3 -alkyl)-2-pyrrolidinyl)isoxazole in high yield, wherein a protected pyrrolidine or 2-oxo-pyrrolidine starting material is reacted with a suitable organic anion and a resulting beta-keto oxime intermediate is cyclized and dehydrated, as well as intermediates useful in the preparation thereof.