Synthesis of N-Acetyl-α-aminobutyric Acid via Amidocarbonylation: A Case Study

Dirk Gördes, Helfried Neumann, Axel Jacobi Von Wangelin, Christine Fischer, Karlheinz Drauz, Hans Peter Krimmer, Matthias Beller

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

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 (<30 mol %) without 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.

Original languageEnglish
Pages (from-to)510-516
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume345
Issue number4
DOIs
StatePublished - Apr 2003
Externally publishedYes

Keywords

  • Amidocarbonylation
  • Amino acids
  • Catalysis
  • N-acetyl-α-aminobutyric acid
  • Palladium

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