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A 11C-Methyl stannane (5-[11C]methyl-1-aza-5-stanna-bicyclo[3.3.3]undecane) for use in palladium-mediated [11C]C–C bond forming reactions with organohalides

✍ Scribed by Tobias Forngren; Linda Samuelsson; Bengt Långström

Publisher
John Wiley and Sons
Year
2004
Tongue
French
Weight
111 KB
Volume
47
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of a ^11^C‐labelled methyl stannane, (5‐[^11^C]methyl‐1‐aza‐5‐stanna‐bicyclo[3.3.3]undecane (2)), and its use in palladium‐mediated Stille reactions to form [^11^C]C–C bonds are described. Stannane 2 was synthesized from iodo[^11^C]methane, 5‐chloro‐1‐aza‐5‐stanna‐bicyclo[3.3.3]undecane 1 and butyl lithium in 20–90% decay‐corrected radiochemical yield starting from iodo[^11^C]methane. Subsequent reaction with a series of substituted aryl and vinyl halides produced the corresponding [^11^C]methylated products 3–5 in up to 90% decay‐corrected radiochemical yield from the crude 2. The total synthesis time, including purification, was 25–30 min from end of radionuclide production. Copyright © 2003 John Wiley & Sons, Ltd.

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