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Synthesis of N ‐Acetyl‐α‐aminobutyric Acid via Amidocarbonylation: A Case Study
Author(s) -
Gördes Dirk,
Neumann Helfried,
von Wangelin Axel Jacobi,
Fischer Christine,
Drauz Karlheinz,
Krimmer HansPeter,
Beller Matthias
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200390059
Subject(s) - chemistry , propionaldehyde , catalysis , palladium , yield (engineering) , phosphine , bromide , acetamide , organic chemistry , uniquac , halide , medicinal chemistry , aldehyde , materials science , activity coefficient , aqueous solution , non random two liquid model , metallurgy
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.