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Synthesis 2017; 49(12): 2733-2742
DOI: 10.1055/s-0036-1558973
paper
© Georg Thieme Verlag Stuttgart · New York

Development of a Method for the Synthesis of 4-Aryl-Functionalized 2-Azabicyclo[3.2.1]octanes

Ian S. Armstrong
a   Department of Chemistry and Biochemistry, Ohio University, 100 University Terrace, Athens, OH 45701, USA
,
Stephen C. Bergmeier*
a   Department of Chemistry and Biochemistry, Ohio University, 100 University Terrace, Athens, OH 45701, USA
b   Edison Biotechnology Institute, Konneker Research Center, Ohio University, 172 Water Tower Drive, Building 25, The Ridges, Athens, OH 45701, USA   Email: bergmeis@ohio.edu
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Publication History

Received: 26 January 2017

Accepted after revision: 28 February 2017

Publication Date:
23 March 2017 (online)

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Abstract

A method for the synthesis of 4-substituted azabicyclo[3.2.1]octanes from N-tosyl-2-azabicyclo[3.2.1]octa-3,6-diene, a versatile bicyclic heterocycle not commonly used in medicinal chemistry research, is presented. The method uses bromination, followed by Suzuki­ coupling, and subsequent reduction and deprotection. The desired 4-substituted azabicyclo[3.2.1]octanes were obtained in moderate to high yields.

Key words

Suzuki coupling - heterocycles - palladium - bicyclic compounds - scaffolds

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1558973.
  • Supporting Information
 

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