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

The synthesis of a ¹¹C‐labelled methyl stannane, (5‐¹¹C]methyl‐1‐aza‐5‐stanna‐bicyclo3.3.3]undecane ( 2 )), and its use in palladium‐mediated Stille reactions to form ¹¹C]C–C bonds are described. Stannane 2 was synthesized from iodo¹¹C]methane, 5‐chloro‐1‐aza‐5‐stanna‐bicyclo3.3.3]undecane 1 and butyl lithium in 20–90% decay‐corrected radiochemical yield starting from iodo¹¹C]methane. Subsequent reaction with a series of substituted aryl and vinyl halides produced the corresponding ¹¹C]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.