Abstract: 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.
Type:
Grant
Filed:
March 30, 2007
Date of Patent:
January 17, 2012
Assignee:
Sunovion Pharmacuticals Inc.
Inventors:
Hang Zhao, Stefan G. Koenig, Charles P. Vandenbossche, Surendra Singh, Harold Scott Wilkinson, Roger P. Bakale