A Concise Synthesis of 6-Oxa-3-azabicyclo[3.1.1]heptane Hydrotosylate

Bridged bicyclic morpholines are important building blocks in medicinal chemistry research. The bicyclic morpholine 6-oxa-3-azabicyclo[3.1.1]heptane (2a) is of particular interest as a morpholine isostere because it is achiral and shows properties similar to that of morpholine based on a derived ana...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 16; pp. 2619 - 2624
Main Authors Wishka, Donn G., Beagley, Paul, Lyon, Jessica, Farley, Kathleen A., Walker, Daniel P.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
3-AZETIDINOLS
bicyclic compounds
heterocycles
stereoselective synthesis
KINASE
alkylation
AGENTS
INHIBITORS
hydrogenation
DERIVATIVES
OXETANES
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Summary:Bridged bicyclic morpholines are important building blocks in medicinal chemistry research. The bicyclic morpholine 6-oxa-3-azabicyclo[3.1.1]heptane (2a) is of particular interest as a morpholine isostere because it is achiral and shows properties similar to that of morpholine based on a derived analogue. The first synthesis of morpholine 2a (tosylate salt) is described. The six-step sequence begins with inexpensive starting materials and uses straightforward chemistry.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1260116