Synthesis 2012; 44(18): 2859-2862
DOI: 10.1055/s-0032-1316748
special topic
© Georg Thieme Verlag Stuttgart · New York

Practical Synthesis of 3-Oxa-6-azabicyclo[3.1.1]heptane Hydrotosylate; A Novel Morpholine-Based Building Block

Daniel P. Walker*, Brian M. Eklov, Matthew W. Bedore
  • Kalexsyn, Inc., 4502 Campus Drive, Kalamazoo, MI 49008, USA, Fax: +1(269)4888490   Email:
Further Information

Publication History

Received: 04 June 2012

Accepted: 22 June 2012

Publication Date:
26 July 2012 (eFirst)


Bridged bicyclic morpholines are important building blocks in medicinal chemistry research. The bicyclic morpholine 3-oxa-6-azabicylo[3.1.1]heptane (3a) is of particular interest as a morpholine isostere because it is achiral and shows similar lipophilicity to that of morpholine, based on the cLogP of a derived analogue. The first synthesis of morpholine 3a (tosylate salt) is described; the seven-step sequence begins with inexpensive starting materials and uses straightforward chemistry.

Supporting Information