TY - JOUR
T1 - Radiosynthesis of 1-iodo-2-[11C]methylpropane and 2-methyl-1-[11C]propanol and its application for alkylation reactions and C―C bond formation
AU - Rotteveel, Lonneke
AU - Poot, Alex J.
AU - Funke, Uta
AU - Pekošak, Aleksandra
AU - Filp, Ulrike
AU - Lammertsma, Adriaan A.
AU - Windhorst, Albert D.
PY - 2017/10/1
Y1 - 2017/10/1
N2 - 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.
AB - 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.
KW - 1-iodo-2-[C]methylpropane
KW - 2-methyl-1-[C]propanol
KW - [C]alkylation
KW - [C]etherification
KW - carbon-11 radiolabelling
KW - positron emission tomography
UR - http://www.scopus.com/inward/record.url?scp=85032192085&partnerID=8YFLogxK
U2 - https://doi.org/10.1002/jlcr.3536
DO - https://doi.org/10.1002/jlcr.3536
M3 - Article
C2 - 28755455
SN - 0362-4803
VL - 60
SP - 566
EP - 576
JO - Journal of Labelled Compounds and Radiopharmaceuticals
JF - Journal of Labelled Compounds and Radiopharmaceuticals
IS - 12
ER -