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Synthesis 2004(3): 446-450  
DOI: 10.1055/s-2004-815937
PAPER
© Georg Thieme Verlag Stuttgart · New York

Improved Procedure for the Selective N-Debenzylation of Benzylamines by Diisopropyl Azodicarboxylate

Jiří Kroutil*, Tomáš Trnka, Miloslav Černý
Department of Organic Chemistry, Charles University, Albertov 6, 128 43 Prague 2, Czech Republic
Fax: +420(221)951326; e-Mail: kroutil@natur.cuni.cz;
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Publication History

Received 5 November 2003
Publication Date:
26 January 2004 (online)

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Abstract

The selective deprotection of N-benzyl group was achieved in the presence of azido, O-benzyl, and N-tosyl groups in reactions of benzylamines derived from 1,6-anhydro-β-d-glucopyranose with diisopropyl azodicarboxylate (DIAD) in THF. The key role of this solvent and the reaction pathway are presented together with proven reaction intermediates.

Key words

protecting groups - debenzylation - cleavage - amines - azides