Radiosynthesis of 1-iodo-2-[11C]methylpropane and 2-methyl-1-[11C]propanol and its application for alkylation reactions and C―C bond formation

Lonneke Rotteveel, Alex J. Poot, Uta Funke, Aleksandra Pekošak, Ulrike Filp, Adriaan A. Lammertsma, Albert D. Windhorst

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The multitude of biologically active compounds requires the availability of a broad spectrum of radiolabeled synthons for the development of positron emission tomography (PET) tracers. The aim of this study was to synthesize 1-iodo-2-[11C]methylpropane and 2-methyl-1-[11C]propanol and investigate the use of these reagents in further radiosynthesis reactions. 2-Methyl-1-[11C]propanol was obtained with an average radiochemical yield of 46 ± 6% d.c. and used with fluorobenzene as starting material. High conversion rates of 85 ± 4% d.c. could be observed with HPLC, but large precursor amounts (32 mg, 333 μmol) were needed. 1-Iodo-2-[11C]methylpropane was synthesized with a radiochemical yield of 25 ± 7% d.c. and with a radiochemical purity of 78 ± 7% d.c. The labelling agent 1-iodo-2-[11C]methylpropane was coupled to thiophenol, phenol and phenylmagnesium bromide. Average radiochemical conversions of 83% d.c. for thiophenol, 40% d.c. for phenol, and 60% d.c. for phenylmagnesium bromide were obtained. In addition, [11C]2-methyl-1-propyl phenyl sulphide was isolated with a radiochemical yield of 5 ± 1% d.c. and a molar activity of 346 ± 113 GBq/μmol at the end of synthesis. Altogether, the syntheses of 1-iodo-2-[11C]methylpropane and 2-methyl-1-[11C]propanol were achieved and applied as proof of their applicability.

Original languageEnglish
Pages (from-to)566-576
Number of pages11
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Issue number12
Publication statusPublished - 1 Oct 2017


  • 1-iodo-2-[C]methylpropane
  • 2-methyl-1-[C]propanol
  • [C]alkylation
  • [C]etherification
  • carbon-11 radiolabelling
  • positron emission tomography

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