Synthesis of deramciclane* labeled with tritium in various positions

János Szammer, Edit Simon-Trompler, Zoltán Banka, József Szúnyog, Imre Klebovich

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Abstract

[(1R)-endo]-(+)-3-bromocamphor was dehalogenated with tritium gas to [3-3H]camphor and via [3-3H]phenylborneol converted to [3-3H]deramciclane isolated as the fumarate salt (specific activity 51.8 GBq/mmol). This three step synthesis from [3-3H]camphor gave an overall yield of 22%. Benzyloxy-acetic acid methyl ester was reduced with sodium-borotritide to 2-benzyloxy-ethanol-[l-3H], and through a four step procedure was converted to 2-dimethylaminoethyl-[2-3H] chloride. The latter was condensed with the sodium derivative of 2-phenylborneol giving rise to [2-dimethylamino-[2-3H]ethoxy]deramciclane isolated as the fumarate (specific activity 8.177 GBq/mmol). This six step synthesis from [ 3H]NaBH4 gave an overall yield of 6%.

Original languageEnglish
Pages (from-to)693-700
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume48
Issue number9
DOIs
Publication statusPublished - Aug 1 2005

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Keywords

  • Anxiolytic agents* 1R,2S,4R-(-)-2-(dimethylaminoethoxy)-2- phenyl-1,7,7-trimethylbicyclo[2.2.1]heptane
  • Tritium
  • [2-dimethylamino-[2-H]ethoxy]deramciclane
  • [3-H]deramciclane

ASJC Scopus subject areas

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

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