Sunovion Pharmaceuticals Inc.

Charles P Vandenbossche

Roger P Bakale

Harold Scott Wilkinson

Surendra Singh

Stefan G Koenig

Hang Zhao

John R Snoonian

Scott H Wilkenson

Surendra P Singh

A convenient method for converting oximes into enamides is disclosed. The process produces enamides without the concomitant production of a large volume of metallic waste.  The enamides are useful precursors to amides and amines.

Enamide process

This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.

Preparation of chiral amides and amines

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Waltham, MA, United States of America

Charles P Vandenbossche