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Synthesis 2009(10): 1659-1662  
DOI: 10.1055/s-0028-1088059
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Straightforward and Scalable Synthesis of Orthogonally Protected 3,7-Diazabicyclo[4.1.0]heptane

Heiko Schramma, Maria Pavlovaa, Christoph Hoenkeb, Jens Christoffers*a
a Institut für Reine und Angewandte Chemie, Universität Oldenburg, Carl von Ossietzky-Str. 9-11, 26111 Oldenburg, Germany
Fax: +49(441)7983873; e-Mail: jens.christoffers@uni-oldenburg.de;
b Boehringer Ingelheim Pharma GmbH & Co. KG, Abteilung Chemische Forschung, Birkendorfer Str. 65, 88397 Biberach an der Riß, Germany
Further Information

Publication History

Received 26 November 2008
Publication Date:
20 April 2009 (online)

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Abstract

Orthogonally N-protected (Boc and Cbz) 3,4-aziridinopiperidine is a versatile building block for the synthesis of 4-substituted 3-aminopiperidines, which are compounds with a high potential for biological activity. A multigram synthesis over five steps, starting with extraordinarily simple materials (pyridine and benzyl chloride), was developed.

Key words

amines - piperidines - aziridines - building blocks - protective groups

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