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

doi:10.1055/s-0032-1316748

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(18): 2859-2862
DOI: 10.1055/s-0032-1316748

special topic

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

Daniel P. Walker*

Kalexsyn, Inc., 4502 Campus Drive, Kalamazoo, MI 49008, USA, Fax: +1(269)4888490 eMail: dpwalker@kalexsyn.com

,

Brian M. Eklov

Kalexsyn, Inc., 4502 Campus Drive, Kalamazoo, MI 49008, USA, Fax: +1(269)4888490 eMail: dpwalker@kalexsyn.com

,

Matthew W. Bedore

Kalexsyn, Inc., 4502 Campus Drive, Kalamazoo, MI 49008, USA, Fax: +1(269)4888490 eMail: dpwalker@kalexsyn.com

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Abstract

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Abstract

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.

Key words

isosteres - bicyclic compounds - heterocycles - cyclization - medicinal chemistry

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Referenzen

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