Process for the preparation of 6,6-dimethyl-3-azabicyclo-[3.3.0]-hexane compounds and enantiomeric salts thereof

US8198463B2 · kind B2 · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• George G. Wu · Berkeley Heights, US
• Frank Xing Chen · Plainsboro, US
• Paitoon Rashatasakhon
• Jeffrey Eckert · Hazlet, US
• George S. K. Wong · Summit, US
• Hong-Chang Lee · Livingston, US
• Nolan C. Erickson · West Orange, US
• Jennifer Ann Vance · San Jose, US
• Peter C. Nirchio · Lebanon, US
• Juergen Weber · Plainsboro, US
• David Jieh-Shyh Tsai · Hackettstown, US
• Nanfei Zou · Fanwood, US

Key dates

• Filing date: Apr 9, 2010
• Grant date: Jun 12, 2012
• Expiry date: Oct 12, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D209/52
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention provides for a process for preparing racemic methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate, its corresponding salt: (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate di-p-toluoyl-D-tartaric acid (“D-DTTA”) salt or a (1S,2R,5R)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate di-p-toluoyl-L-tartaric acid salt (“L-DTTA”) in a high enantiomeric excess. This invention also provides for a process for preparing a (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate dibenzoyl-D-tartaric acid (“D-DBTA”) salt or a (1S,2R,5R)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate L-tartaric acid (“L-DBTA”) salt in a high enantiomeric excess. Further, this invention provides a process for preparing intermediates II, IIB, III, IV, IV salt, V, VI, and VII.