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3β-(p-Trimethylsilylphenyl)tropane-2β-carboxylic acid methyl ester: A new precursor for the preparation of [123I]RTI-55

✍ Scribed by John L. Musachio; Kathryn I. Keverline; F.Ivy Carroll; Robert F. Dannals

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
295 KB
Volume
47
Category
Article
ISSN
0969-8043

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✦ Synopsis

Here we report the synthesis of 3 beta-(p-trimethylsilylphenyl)tropane-2 beta-carboxylic acid methyl ester, a new, easily prepared precursor for the synthesis of radioiodinated versions of RTI-55. In contrast to the 3 beta-(p-trimethylstannylated) precursor for radioiodination, the aryl silane is prepared directly by the 1,4 addition of p-trimethylsilylphenylmagnesium iodide to anhydroecgonine methyl ester in 49% yield (Scheme 1). Radioiododesilylation proceeded smoothly (approx. 85% radioincorporation after 15 min at room temperature) using 1 microgram of the novel precursor in trifluoroacetic acid and chloramine-T as oxidant. Isolated radiochemical yields for 125I and 123I radiolabelings were 72 and 48%, respectively, with a calculated specific activity for [123I]RTI-55 of > 2000 mCi/mumol.

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