Schering Corporation

Merck Sharp + Dohme Corp.

Nolan C Erickson

George G Wu

Frank Xing Chen

Nanfei Zou

George S Wong

Jeffrey Manning Eckert

Hong-Chang Lee

George S K Wong

David Jieh-Shyh Tsai

Juergen Weber

Peter C Nirchio

Paitoon Rashatasakhon

Jennifer Ann Vance

Jeffrey M Eckert

Zou Nanfei

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 (&#x201c;D-DBTA&#x201d;) salt or a (1S,2R,5R)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate L-tartaric acid (&#x201c;L-DBTA&#x201d;) 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.

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

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: (2S, 3R, 4S)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate di-p-toluoyl-D-tartaric acid ('D-DTTA') salt or a (2R, 3S, 4R)-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 (2S, 3R, 4S)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate dibenzoyl-D-tartaric acid (&#x201c;D-DBTA&#x201d;) salt or a (2R, 3S, 4R)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylate L-tartaric acid (&#x201c;L-DBTA&#x201d;) 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.

Process for the preparation of 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds and enantiomeric salts thereof

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West Orange, NJ, United States of America

Nolan C Erickson