A One-Pot Preparation of 1,3-Disubstituted Azetidines

Michael C. Hillier*† and Cheng-yi Chen
Department of Process Research, Merck & Co., P.O. Box 2000, Rahway, New Jersey 07065 michael_hillier@merck.com
J. Org. Chem., 2006, 71 (20), pp 7885–7887
DOI: 10.1021/jo061147x
Publication Date (Web): September 7, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Current address:  Abbott Laboratories, North Chicago, IL 60064.

Abstract

Abstract Image

A straightforward synthesis of 1,3-disubstituted azetidines has been accomplished via the alkylation of a primary amine with the bis-triflate of a 2-substituted-1,3-propanediol species. This transformation is carried out in one reaction vessel, and elimination of the alkylating reagent is generally not a major byproduct. The scope of this methodology has been investigated using a variety 2-substituted-1,3-propanediols and amine nucleophiles.

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History

  • Published In Issue September 29, 2006
  • Received June 5, 2006

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