Discovery, implementation, and mechanism of a pressure-dependent catalytic, asymmetric α,β-unsaturated carboxylic acid hydrogenation

ORGN 408

David M. Tellers, david_tellers@merck.com1, J. Chris McWilliams1, Guy Humphrey1, Michel Journet1, and Yongkui Sun2. (1) Department of Process Research and the Catalysis and Reaction Discovery and Development Lab, Merck and Co., Inc, PO Box 2000, Rahway, NJ 07065-0900, (2) Department of Process Research and the Catalysis and Reaction Discovery and Development Lab, Merck & Co., Inc, PO Box 2000, Rahway, NJ 07065-0900
The asymmetric hydrogenation of α,β-unsaturated carboxylic acids is a useful method for preparing chiral carboxylic acid derivatives. Towards that end, we sought to incorporate the hydrogenation of an α,β-unsaturated carboxylic acid into one of our processes (eq 1). This presentation will describe the discovery and ultimate implementation of this hydrogenation on pilot plant scale. A mechanistic description to explain the unusual reaction pressure dependence, along with supporting experimental results, will be highlighted.

 

Process R&D, Practical Synthesis, and Methodology
1:00 PM-4:20 PM, Tuesday, 15 March 2005 Convention Center -- Room 11A, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005