Synthesis of Long‐Chain 3‐Alkylpyrroles Bearing Terminal Carboxy or Amino Groups
Authors:
- 23 September 2005
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 88 (9) , 2470-2478
Abstract
Two new ω‐(1H‐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 NaBH3CN in glacial AcOH was observed, for which a plausible mechanism is proposed (Scheme 3).Keywords
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