Synthesis of potential metabolites of the brain imaging agents methyl (1 R ,2 S ,3 S ,5 S )‐3‐(4‐Iodophenyl)‐8‐alkyl‐8‐azabicyclo[3.2.1]octane‐2‐carboxylate

The synthesis of potential hydroxy metabolites of the brain imaging agents methyl (1 R ,2 S ,3 S ,5 S )‐3‐(4‐iodophenyl)‐8‐methyl‐8‐azabicyclo[3.2.1]octane‐2‐carboxylate and methyl (1 R ,2 S ,3 S ,5 S )‐3‐(4‐iodophenyl)‐8‐(3‐fluoropropyl)‐8‐azabicyclo[3.2.1]octane‐2‐carboxylate are reported. The nitration of iodophenyltropanes 1 or 2 with nitronium tetrafluoroborate afforded the nitro compounds 3 or 4 which were reduced with iron powder to the corresponding amino compounds 5 and 6 . The final hydroxylated products 7 and 8 were obtained via a modified Sandmeyer reaction.