The reductive cleavage of cyclic aminol ethers to N,N-dialkylaminoderivatives: Modifications to the Eschweiler-Clarke procedure

Philip C. Bulman Page, Harry Heaney, Gerasimos A. Rassias, Serge Reignier, Edward P. Sampler, Salem Talib

Research output: Contribution to journalArticlepeer-review

Abstract

The reductive cleavage of cyclic aminol ethers to give N-alkylamino- derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.
Original languageEnglish
Pages (from-to)104-106
Number of pages3
JournalSynlett
Issue number1
Publication statusPublished - 2000

Keywords

  • ring opening
  • chlorotrimethylsilane
  • SECONDARY
  • 1
  • sodium cyanoborohydride
  • ASYMMETRIC-SYNTHESIS
  • reductive
  • 3-OXAZOLIDINES
  • chiral heterocycles
  • aminol ethers

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