Preparation of a small library of secondary amino acids was achieved by solution-phase organic synthesis using reductive amination reactions with selected cc-amino acids and aromatic aldehydes. Reductive amination employing sodium triacetoxyborohydride instead of sodium cyanoborohydride was found to give shorter reaction times and much safer byproducts. With less sterically hindered a-amino acids, direct reductive amination generally yielded the bisalkylated product. However, monoalkylation was achieved by adopting an indirect reductive amination route. Reaction mixtures were characterized by HPLC and LC-MS, resulting in the synthesis of a 21 compound library.
Library of Congress Subject Headings
Amination; Amino acids--Synthesis; Organic compounds--Synthesis
Department, Program, or Center
School of Chemistry and Materials Science (COS)
D'Souza, Rohini, "Reductive amination of (alpha) - amino acids: Solution - Phase synthesis" (2001). Thesis. Rochester Institute of Technology. Accessed from
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