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Synthesis 2012; 44(21): 3387-3391
DOI: 10.1055/s-0032-1316789
paper
© Georg Thieme Verlag Stuttgart · New York

Improved Synthesis of No-Carrier-Added [*I]MIBG and Its Precursor

Friedrich Hammerschmidt*
a   Institute of Organic Chemistry, University of Vienna, Währingerstraße 38, 1090 Vienna, Austria   Fax: +43(1)42779521   Email: friedrich.hammerschmidt@univie.ac.at
,
Herbert Kvaternik*
b   Department of Nuclear Medicine, Medical University of Graz, Auenbruggerplatz 9, 8036 Graz, Austria   Fax: +43(316)38512151   Email: herbert.kvaternik@medunigraz.at
c   Radiopharmaceuticals, Seibersdorf Labor GmbH, 2444 Seibersdorf, Austria
,
Anna Schweifer
a   Institute of Organic Chemistry, University of Vienna, Währingerstraße 38, 1090 Vienna, Austria   Fax: +43(1)42779521   Email: friedrich.hammerschmidt@univie.ac.at
,
Kurt Mereiter
d   Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, 1060 Vienna, Austria
,
Reingard M. Aigner
b   Department of Nuclear Medicine, Medical University of Graz, Auenbruggerplatz 9, 8036 Graz, Austria   Fax: +43(316)38512151   Email: herbert.kvaternik@medunigraz.at
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Further Information

Publication History

Received: 09 July 2012

Accepted after revision: 10 September 2012

Publication Date:
28 September 2012 (online)

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† Deceased December 29, 2010

Abstract

3-(Trimethylstannyl)benzyl alcohol was coupled in a Mitsunobu reaction with bis(Boc)-guanidine to give bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine used as precursor for [*I]MIBG. Radioiodination with [131I]iodine generated from [131I]NaI and chloramine-T, removal of Boc groups, and purification by HPLC gave no-carrier-added tracer [*I]MIBG (81% radiochemical yield, 99% chemical purity) used for imaging tumors of neuroendocrine origin. The structures of bis(Boc)-guanidine and bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine were secured by single crystal X-ray structure analyses.

Key words

Mitsunobu reaction - electrophilic aromatic substitution - medicinal chemistry - [131I]iodine - halogenation
 

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