Synlett 2012; 23(12): 1779-1782
DOI: 10.1055/s-0031-1290698
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© Georg Thieme Verlag Stuttgart · New York

An Optimised Synthesis of 2-[2,3-Bis(tert-butoxycarbonyl)guanidino]ethylamine

Authors

  • Shane M. Hickey

    Centre for Biotechnology, Chemistry and Systems Biology, School of Life and Environmental Sciences, Deakin University, Waurn Ponds, Victoria, 3216, Australia, Fax: +61(3)52271040   Email: fred.pfeffer@deakin.edu.au
  • Trent D. Ashton

    Centre for Biotechnology, Chemistry and Systems Biology, School of Life and Environmental Sciences, Deakin University, Waurn Ponds, Victoria, 3216, Australia, Fax: +61(3)52271040   Email: fred.pfeffer@deakin.edu.au
  • Simren K. Khosa

    Centre for Biotechnology, Chemistry and Systems Biology, School of Life and Environmental Sciences, Deakin University, Waurn Ponds, Victoria, 3216, Australia, Fax: +61(3)52271040   Email: fred.pfeffer@deakin.edu.au
  • Frederick M. Pfeffer*

    Centre for Biotechnology, Chemistry and Systems Biology, School of Life and Environmental Sciences, Deakin University, Waurn Ponds, Victoria, 3216, Australia, Fax: +61(3)52271040   Email: fred.pfeffer@deakin.edu.au
Further Information

Publication History

Received: 13 April 2012

Accepted after revision: 14 May 2012

Publication Date:
04 July 2012 (online)


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Abstract

This short report describes an improved, reliable, and high-yielding (>90%) synthesis of 2-[2,3-bis(tert-butoxycarbonyl)guanidino]ethylamine. The method is scalable (>5 g), and the product obtained directly from the reaction mixture requires no further purification. In addition, this methodology can be successfully applied to other diamine substrates (1,3-propyl and 1,4-butyl; 70% and 61% yield, respectively).

Supporting Information