Efficient Synthesis of Orthogonally Protected Spermidine and Norspermidine Derivatives

Abstract

Several orthogonally protected spermidine and norspermidine derivatives have been synthesized via cyanoethylation of monoprotected 1,4‐butanediamine (putrescine) or 1,3‐propanediamine followed by protection of their secondary amino groups and final reduction of the nitriles with lithium aluminum hydride in etheral solution at 0°C, thus affording protected norspermidine or spermidine that may be used in the synthesis of polyamine amides or may be further functionalized.

Keywords:

• Michael addition
• polyamines
• protecting groups
• reduction

Acknowledgment

The authors are indebted to the Faculty of Chemistry, Gdańsk University of Technology, for financial support.