Improved synthesis of 13C,2H3- and 2H3-salmeterol by Cs2CO3-mediated monoalkylation of a primary amine

Tadeusz F. Molinski, Scott D Stanley

Research output: Contribution to journalArticle

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Abstract

An abbreviated synthesis of isotopically labelled salmeterol has been achieved. The key improvement utilizes a highly selective Cs2CO3-mediated one-pot alkylation of benzylamine by 6-bromo-1-(4′-phenylbutoxy)hexane to prepare the limiting reagent, 6-N-benzylamino-1-(4′-phenylbutoxy)hexane without overalkylation. The method was applied to synthesis of the title compounds in >97 at% isotopic purity.

Original languageEnglish (US)
Pages (from-to)755-762
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume45
Issue number9
DOIs
StatePublished - Aug 2002

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Keywords

  • Bronchodilator
  • Carbon-13
  • Deuterium
  • Mass spectrometry
  • Phenethylamine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Clinical Biochemistry
  • Molecular Medicine
  • Pharmacology

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