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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
Author(s) -
Andersen Annette,
Wang Shaoyin,
Thompson Robert D.,
Neumeyer John L.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340541
Subject(s) - chemistry , nitration , octane , carboxylate , bicyclic molecule , alkyl , medicinal chemistry , stereochemistry , nitro , organic chemistry
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.