Solid-phase synthesis of hydroxypiperazine derivatives using phenethylamine linker by oxidation-Cope elimination

Jin Soo Seo, Hye Won Kim, Min Yoon Cheol, Chan Ha Deok, Young Dae Gong

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A general method is reported for the parallel solid-phase synthesis of hydroxypiperazine derivatives based on the oxidation-Cope elimination of polymer-bound phenethylamine linker with m-CPBA. The key intermediate of phenethylamine N-oxide resins was separable on solid-phase for subsequent β-elimination, from which the desired hydroxypiperazine products could be obtained in high purities and yields without any significant contamination at 90°C for 2 h. The utility of the methodology for solid-phase synthesis of general hydroxylamines was also investigated using the same linker. The progress of reactions could be monitored on polymer bound intermediates by ATR-FTIR spectroscopy on single bead. The desired products were obtained in good six-step overall yields upon cleavage from the resins and were characterized by LC/MS, 1H NMR, and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)9305-9311
Number of pages7
JournalTetrahedron
Volume61
Issue number39
DOIs
Publication statusPublished - 2005 Sep 26

Keywords

  • Hydroxypiperazine
  • Oxidation-Cope
  • Phenethylamine linker
  • Solid-phase

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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