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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