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Synthesis 2004(7): 1033-1036  
DOI: 10.1055/s-2004-822329
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Regioisomeric Azidobutanediols

Marion Aepkers, Bernhard Wünsch*
Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhelms-Universität Münster, Hittorfstraße 58-62, 48149 Münster, Germany
Fax: +49(251)8332144; e-Mail: wuensch@uni-muenster.de;
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Publikationsverlauf

Received 19 January 2004
Publikationsdatum:
02. April 2004 (online)

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Abstract

Investigations to control the regioselectivity during the acetalization of pivalaldehyde (7) with butane-1,2,4-triol (4) were performed. Thermodynamic control led to the regioisomeric acetals 8 and 9 in the ratio 76:24, whereas kinetic control favored the five-membered acetal 9 (8/9 30:70). Tosylation, nucleophilic substitution with NaN3, and subsequent methanolysis of the regioisomeric acetals 8 and 9 provided the regioisomeric 4-azidobutanediols 5 and 6, which are considered as valuable building blocks for the synthesis of novel NMDA-receptor antagonists.

Key words

acetals - azides - regioselectivity - medicinal chemistry - NMDA-antagonists

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