Abstract
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
Publication Date
7-1-2001
Document Type
Thesis
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Advisor
Turner, Kay
Recommended Citation
D'Souza, Rohini, "Reductive amination of (alpha) - amino acids: Solution - Phase synthesis" (2001). Thesis. Rochester Institute of Technology. Accessed from
https://repository.rit.edu/theses/6036
Campus
RIT – Main Campus
Comments
Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works. Physical copy available through RIT's The Wallace Library at: QD281.A6 D768 2001