H. Parnes et Ej. Shelton, SYNTHESIS OF (R)-3-AMINOQUINUCLIDINE-[3-C-14] AND (S)-3-AMINOQUINUCLIDINE-[3-C-14] ENANTIOMERS, IMPORTANT COMPONENTS OF A VARIETY OF 5-HT3 LIGANDS, Journal of labelled compounds & radiopharmaceuticals, 38(1), 1996, pp. 19-29
Citations number
11
Categorie Soggetti
Chemistry Analytical","Pharmacology & Pharmacy","Biochemical Research Methods
3-Aminoquinuclidine, an important fragment associated with many 5-HT (
serotonin) receptor ligands, has been synthesized using a C-14- carbon
ation based sequence to prepare the starting material, isonicotinic C-
14-acid (6). Elaboration of (6) to alpha-bromoacetyl-[C-14] isonipecot
ic acid (10) via the corresponding diazoketone, followed by intamolecu
lar cyclization, gave the key intermediate 3-quinuclidone-[3-C-14] (3)
. 3-quinuclidone-[3-C-14] was converted to a mixture of phenethylamine
diastereomers. Carrier free crystallization and hydrogenolysis furnis
hed both (R) and (S) 3-aminoquinuclidine-[3-C-14] enantiomers at >99%
optical purity.