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

Heiko Schramm; Maria Pavlova; Christoph Hoenke; Jens Christoffers

doi:10.1055/s-0028-1088059

PAPER

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

Heiko Schramm^a, Maria Pavlova^a, Christoph Hoenke^b, 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

Abstract

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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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