Sulfinamides as Highly Effective Amine Protecting Groups and Their Use in the Conversion of Amino Alcohols into Morpholines

Sven P. Fritz, Amara Mumtaz, Muhammad Yar, Eoghan M. McGarrigle, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

30 Citations (Scopus)

Abstract

1,2-Amino alcohols have been converted into morpholines by using sulfinamides as temporary protecting/activating groups on the amine. We have developed a procedure for the selective synthesis of monoprotected N-sulfinyl amino alcohols through a double sulfinylation/hydrolysis strategy. Following the reaction of the sulfinamides with bromoethyl-diphenylsulfonium triflate, protected morpholines were obtained in high yields. Subsequent treatment with HCl liberated the morpholine hydrochloride salts. The usefulness of this high yielding and efficient methodology has been demonstrated in the formal synthesis of the antidepressant drug (S,S)-reboxetine.

Original languageEnglish
Pages (from-to)3156-3164
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Jun 2011

Keywords

  • Nitrogen heterocycles
  • Amino alcohols
  • Sulfinamides
  • Annulation
  • Protecting groups
  • VINYL SULFONIUM SALTS
  • ASYMMETRIC-SYNTHESIS
  • TERT-BUTANESULFINAMIDE
  • SULFURYL CHLORIDE
  • STEREOSELECTIVE-SYNTHESIS
  • TOLUENESULFINIC ESTERS
  • SULFINYL CHLORIDES
  • CONVENIENT METHOD
  • TANDEM REACTIONS
  • DERIVATIVES

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