Synthesis of deramciclane labelled with radiocarbon in various positions

J. Szammer, E. Simon-Trompler, J. Máté, M. Abermann, I. Ürmös, I. Klebovich

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Abstract

[U-14C]Bromobenzene, prepared from [14C]barium carbonate according to literature procedures, was transformed (Li/diethylether) into [14C]phenyllithium which was condensed with camphor giving rise to [U-14C-phenyl]borneol: 2. The latter, after conversion into its sodium sail, was reacted with dimethylaminoethyl chloride to give [14C-Ar]Deramciclane, which was isolated as the fumarate salt. This 8 step synthesis from [14C]BaCO3 gave an overall yield of 12%. [1-14C]Sodium acetate, through a standard 5 step literature procedure, was converted to N,N-dimethylaminoethyl-1-14C chloride 5 which was condensed with the sodium derivative of 2-phenylborneol giving rise to [1-14C-side chain]Deramciclane, again isolated as the fumarate. This 6 step synthesis from [14C]BaCO3 gave an overall yield of 8%. The specific radioactivities from the two syntheses were respectively 40 mCi/mmol and 21 mCi/mmol; chemical and radiochemical purities were better than 98%.

Original languageEnglish
Pages (from-to)1011-1018
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume39
Issue number12
DOIs
Publication statusPublished - Dec 1 1997

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Keywords

  • 1R,2S,4R-(-)-2-(dimethylaminoethoxy)-2-phenyl-1,7,7 -trimethylbicyclo[2.2.1]heptane
  • Anxiolytic agents
  • Carbon-14
  • [1-C-side chain]Deramciclane
  • [U-C-phenyl]Deramciclane

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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