Synthesis 2002(15): 2195-2202
DOI: 10.1055/s-2002-34859
PAPER
© Georg Thieme Verlag Stuttgart · New York

Selective Synthesis of Carbamate Protected Polyamines Using Alkyl Phenyl Carbonates

Michael Pittelkow, Rasmus Lewinsky, Jørn Bolstad Christensen*
Chemical Laboratory II, The H. C. Ørsted Institute, University of Copenhagen, Universitetsparken 5, 2100 Denmark
Fax: +45(353)20212 ; e-Mail: jbc@kiku.dk;
Further Information

Publication History

Received 27 May 2002
Publication Date:
21 October 2002 (online)

Abstract

Utilising alkyl phenyl carbonates, an economical, practical and versatile method for selective Boc, Cbz and Alloc protection of polyamines has been developed. This method allows Boc, Cbz and Alloc protection of primary amines in the presence of secondary amines by reaction of the polyamines with the alkyl phenyl carbonates. Also, this method allows mono carbamate protection of simple symmetrical aliphatic α,ω-alkanediamines in high yields with respect to the diamine. Finally, the method allows selective carbamate protection of a primary amine located on a primary carbon in the presence of a primary amine located on a secondary or a tertiary carbon in excellent yields.

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