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Synthesis 2009(2): 283-289  
DOI: 10.1055/s-0028-1083290
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Method for the Selective Protection of Aromatic Amines in the Presence of Aliphatic Amines

Valérie Perron, Shaun Abbott, Nancie Moreau, Devin Lee, Christopher Penney, Boulos Zacharie*
ProMetic BioSciences Inc., Suite 150, 500 Cartier Blvd. W., Laval, QC, H7V 5B7, Canada
Fax: +1(450)7811403; e-Mail: b.zacharie@prometic.com;
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Publication History

Received 18 July 2008
Publication Date:
19 December 2008 (online)

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Abstract

A simple and efficient procedure has been developed for the regioselective protection of aromatic amines in the presence of aliphatic amines. The method is general for the preparation of mono-N-Boc, -N-Cbz, -N-Fmoc or -N-Alloc aromatic amines in high yield without affecting the aliphatic amines. This approach is applicable to substituted (aminoalkyl)aniline compounds with different functionalities and was employed to supply gram quantities of the protected aniline product.

Key words

amines - carbamates - protecting groups - protonations - regioselectivity

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