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Synthesis of [1-11C]propyl and [1-11C]butyl iodide from [11C]carbon monoxide and their use in alkylation reactions

✍ Scribed by Jonas Eriksson; Gunnar Antoni; Bengt Långström

Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
184 KB
Volume
49
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A method to prepare [1‐^11^C]propyl iodide and [1‐^11^C]butyl iodide from [^11^C]carbon monoxide via a three step reaction sequence is presented. Palladium mediated formylation of ethene with [^11^C]carbon monoxide and hydrogen gave [1‐^11^C]propionaldehyde and [1‐^11^C]propionic acid. The carbonylation products were reduced and subsequently converted to [1‐^11^C]propyl iodide. Labelled propyl iodide was obtained in 58±4% decay corrected radiochemical yield and with a specific radioactivity of 270±33 GBq/µmol within 15 min from approximately 12 GBq of [^11^C]carbon monoxide. The position of the label was confirmed by ^13^C‐labelling and ^13^C‐NMR analysis. [1‐^11^C]Butyl iodide was obtained correspondingly from propene and approximately 8 GBq of [^11^C]carbon monoxide, in 34±2% decay corrected radiochemical yield and with a specific radioactivity of 146±20 GBq/µmol. The alkyl iodides were used in model reactions to synthesize [O‐propyl‐1‐^11^C]propyl and [O‐butyl‐1‐^11^C]butyl benzoate. Propyl and butyl analogues of etomidate, a β‐11‐hydroxylase inhibitor, were also synthesized. Copyright © 2006 John Wiley & Sons, Ltd.

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