Synthesis of N-Acetyl-α-aminobutyric Acid via Amidocarbonylation: A Case Study
The synthesis of N-acetyl-α-aminobutyric acid by amidocarbonylation of propionaldehyde with acetamide in the presence of palladium catalysts is studied in detail. The influence of various reaction conditions and compositions (e.g., the co-catalysts acid and bromide) on the yield of N-acetyl-α-aminobutyric acid is shown. For the first time it is demonstrated that the palladium-catalyzed amidocarbonylations of aldehydes can be run with significantly lower halide concentrations (a major yield decrease. While phosphine-free catalyst systems give best yields at low CO pressure, phosphine-ligated palladium catalysts lead to better yields at higher CO pressure. At low palladium loadings (0.1 mol %), unwanted condensation reactions of propionaldehyde become increasingly competitive.
Goerdes, Dirk,Neumann, Helfried,Von Wangelin, Axel Jacobi,Fischer, Christine,Drauz, Karlheinz,Krimmer, Hans-Peter,Beller, Matthias
p. 510 - 516
(2007/10/03)
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