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

✍ Scribed by Annette Andersen; Shaoyin Wang; Robert D. Thompson; John L. Neumeyer


Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
305 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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.


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