Synthesis of ene-trifluoroacetamides and subsequent reduction to chiral acetamides

ORGN 612

Elizabeth A. Secord1, J. Christopher McWilliams2, Shawn P. Allwein1, Todd D. Nelson1, Michael H. Kress1, and David L. Hughes3. (1) Department of Process Research, Merck Research Laboratories, 466 Devon Park Drive, WYN-3, Wayne, PA 19087, (2) Process Research, Merck Research Laboratories, PO Box 2000, Rahway, NJ 07065-0900, (3) Department of Process Research, Merck & Co., Inc, RY800-B369 P.O. Box 2000, Rahway, NJ 07065
The synthesis of ene-trifluoroacetamides from the aryl ketone proceeds through the corresponding oxime quantitatively. The oxime is converted to the enamide in high yield through an iron mediated acylation. Finally, an efficient reduction of the enamides to the corresponding chiral acetamides has been developed. The trifluoroacetate protecting group provides a mild deprotection for convenient access to the chiral amines.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004