Abstract
3-Aminoquinuclidine, an important fragment associated with many 5-HT (serotonin) receptor ligands, has been synthesized using a 14C-carbonation based sequence to prepare the starting material, isonicotinic 14C-acid (6). Elaboration of (6) to α-bromoacetyl-[14C] isonipecotic acid (10) via the corresponding diazoketone, followed by intamolecular cyclization, gave the key intermediate 3-quinuclidone-[3-14C] (3). 3-quinuclidone-[3-14C] was converted to a mixture of phenethylamine diastereomers. Carrier free crystallization and hydrogenolysis furnished both (R) and (S) 3-aminoquinuclidine-[3-14C] enantiomers at >99% optical purity.
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