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Radiosynthesis of 1‐iodo‐2‐[ 11 C]methylpropane and 2‐methyl‐1‐[ 11 C]propanol and its application for alkylation reactions and C―C bond formation
Author(s) -
Rotteveel Lonneke,
Poot Alex J.,
Funke Uta,
Pekošak Aleksandra,
Filp Ulrike,
Lammertsma Adriaan A.,
Windhorst Albert D.
Publication year - 2017
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3536
Subject(s) - chemistry , radiosynthesis , phenylmagnesium bromide , yield (engineering) , thiophenol , alkylation , bromide , chemical synthesis , radiochemistry , medicinal chemistry , nuclear chemistry , reagent , organic chemistry , catalysis , biochemistry , materials science , microbiology and biotechnology , in vivo , metallurgy , in vitro , biology
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‐[ 11 C]methylpropane and 2‐methyl‐1‐[ 11 C]propanol and investigate the use of these reagents in further radiosynthesis reactions. 2‐Methyl‐1‐[ 11 C]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‐[ 11 C]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‐[ 11 C]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, [ 11 C]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‐[ 11 C]methylpropane and 2‐methyl‐1‐[ 11 C]propanol were achieved and applied as proof of their applicability.