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Synthesis 1996; 1996(4): 452-454
DOI: 10.1055/s-1996-4245
short paper
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Convenient Preparation of Optically Active N,N’-Disubstituted Piperazines from Various (S)-α-Amino Acid Esters

Masaaki Watanabe, Yoshitane Kojima* , Kenji Kawabe, Eiji Hatamoto, Eiji Tsuru, Hiroyuki Miyake, Tetsushi Yamashita1
  • *Department of Chemistry, Faculty of Science, Osaka City University, Sugimoto, Sumiyoshi-ku, Osaka 558, Japan, Fax +81(6)6052522
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Publication Date:
31 December 2000 (online)

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N,N,N’,N’-Diethylene bis-(S)-α-amino acid diester dihydrochlorides (piperazine derivatives) were prepared in 70-80% yield by the reaction of 1 mol equivalent of N,N’-monoethylene-bis(S)-α-amino acid diester dihydrochloride with 1 mol equivalent of glyoxal in the presence of 2 mol equivalents of sodium cyanoborohydride in methanol. The precursors used were also obtained similarly from (S)-α-amino acid ester hydrochlorides using glyoxal and sodium cyanoborohydride in 70-80% yield.

piperazines - sodium cyanoborohydride - glyoxal - α-amino acids - reductive N-alkylation

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