A Concise Synthetic Method for Constructing 3-Substituted Piperazine-2-Acetic Acid Esters from 1,2-Diamines

Authors

Srinivas Chamakuri
Sunny Ann Tang
Kevin A Tran
Shiva Krishna Reddy Guduru
Peter K Bolin
Kevin R MacKenzie
Damian W Young

Publication Date

5-25-2022

Journal

Molecules

DOI

10.3390/molecules27113419

PMID

35684357

PMCID

PMC9182393

PubMedCentral® Posted Date

5-25-2022

PubMedCentral® Full Text Version

Post-print

Published Open-Access

yes

Keywords

Acetic Acid, Diamines, Esters, Piperazine, Piperazines, Stereoisomerism, chiral piperazines; 2, 3-substituted piperazines; diamine; annulation; masamune condensation

Abstract

We report a short synthetic route for synthesizing 2,3-substituted piperazine acetic acid esters. Optically pure amino acids were efficiently converted into 1,2-diamines that could be utilized to deliver the title 2,3-substituted piperazines in five steps with a high enantiomeric purity. The novel route facilitated, for the first time, the synthesis of 3-phenyl substituted-2-piperazine acetic acid esters that were difficult to achieve using other methods; however, in this case, the products underwent racemization.

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