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A new approach for 11C–C bond formation: Synthesis of 17α-(3′-[11C]prop-1-yn-1-yl)-3-methoxy-3,17β-estradiol

✍ Scribed by F. Wüst; J. Zessin; B. Johannsen

Publisher: John Wiley and Sons
Year: 2003
Tongue: French
Weight: 200 KB
Volume: 46
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.674

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✦ Synopsis

Abstract

A new approach for ^11^C–C bond formation via a Sonogashira‐like cross‐coupling reaction of terminal alkynes with [^11^C]methyl iodide was exemplified by the synthesis of 17__α__‐(3′‐[^11^C]prop‐1‐yn‐1‐yl)‐3‐methoxy‐3,17__β__‐estradiol. The LC‐purified title compound was obtained in decay‐corrected radiochemical yields of 27–47% (n=8) based on [^11^C]methyl iodide within 21–27 min after EOB. In a typical synthesis starting from 9.6 GBq [^11^C]methyl iodide, 1.87 GBq of 17__α__‐(3′‐[^11^C]prop‐1‐yn‐1‐yl)‐3‐methoxy‐3,17__β__‐estradiol was synthesized in radiochemical purity >99%. The specific radioactivity ranged between 10 and 19 GBq/µmol, and the labeling position was verified by ^13^C‐NMR analysis of the corresponding ^13^C‐labeled compound. Copyright © 2003 John Wiley & Sons, Ltd.

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