Ceric ammonium nitrate impregnated on silica gel in the removal of thetert-butoxycarbonyl group

Jih Ru Hwu*, Moti L. Jain, Fu Yuan Tsai, A. Balakumar, G. H. Hakimelahi, Shwu Chen Tsay

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

10 Scopus citations

Abstract

The tert-butoxycarbonyl group was efficiently (80-99% yields) removed from an amino, hydroxy, or mercapto functionality in organic compounds by use of 0.20 equiv of Ce(NH4)2(NO3)6 in acetonitrile at reflux. Application of the solid-supported reagent involving the use of 0.20 equiv of Ce(NH4)2(NO3)6 impregnated on silica gel in toluene at reflux gave the deprotected products in 90-99% yields. These reactions likely proceed through an electron transfer process.

Original languageEnglish
Pages (from-to)28-36
Number of pages9
JournalArkivoc
Volume2002
Issue number9
StatePublished - 2002
Externally publishedYes

Keywords

  • Amino ester
  • Ceric ammonium nitrate
  • Deprotection
  • Silica gel
  • tert-butoxycarbonyl

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