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Synthesis of Long-Chain 3-Alkylpyrroles Bearing Terminal Carboxy or Amino Groups

✍ Scribed by José M. Freitas; Luísa M. Abrantes; Tamis Darbre

Publisher: John Wiley and Sons
Year: 2005
Tongue: German
Weight: 122 KB
Volume: 88
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200590183

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✦ Synopsis

Abstract

Two new ω‐(1__H__‐pyrrol‐3‐yl)alkanoic acids 8a,b and the corresponding amines 9a,b were prepared on large scale in 41–51 and 27–39% overall yield, respectively, starting from N‐phenylsulfonyl‐protected pyrrole. The target compounds contain the desired functional groups for attachment of biomolecules such as proteins. During synthesis, an unprecedented partial reduction of the pyrrole ring with NaBH~3~CN in glacial AcOH was observed, for which a plausible mechanism is proposed (Scheme 3).

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