Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates

• Yasui Eiko

  Department of Applied Chemistry, Kogakuin University Department of Chemistry and Life Science, Kogakuin University

• Tsuda Jyunpei

  Department of Applied Chemistry, Kogakuin University

• Ohnuki Satoshi

  Department of Applied Chemistry, Kogakuin University

• Nagumo Shinji

  Department of Applied Chemistry, Kogakuin University Department of Chemistry and Life Science, Kogakuin University

Abstract

Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxylate is protected with a benzyl group, selective mono-reduction does not occur. Considering that furan-2,5-dicarboxylates did not give the corresponding mono-alcohol under the same conditions, the unprotected nitrogen atom of pyrrole apparently plays an important role in this selective mono-reduction.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 64 (9), 1262-1267, 2016

  The Pharmaceutical Society of Japan

Keywords

• pyrrole dicarboxylate
• diisobutylaluminum hydride (DIBAH)
• selective reduction

Details

• CRID: 1390282679153183360
• NII Article ID: 130005261571
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c16-00122
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 027565159
• PubMed: 27581630
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I027565159
• Web Site: https://www.jstage.jst.go.jp/article/cpb/64/9/64_c16-00122/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed