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Synthesis of (R) and (S) 3-aminoquinuclidine-[3-14C] enantiomers, important components of a variety of 5-HT3 ligands

✍ Scribed by Howard Parnes; Emma J. Shelton

Publisher: John Wiley and Sons
Year: 1996
Tongue: French
Weight: 460 KB
Volume: 38
Category: Article
ISSN: 0022-2135
DOI: 10.1002/(sici)1099-1344(199601)38:1<19::aid-jlcr805>3.0.co;2-d

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✦ Synopsis

3-Aminoquinuclidine, an important fragment associated with many 5-HT (serotonin) receptor ligands, has been synthesized using a 14Ccarbonation based sequence to prepare the starting material, isonicotinic 14C-acid (6). Elaboration of (6) to a-br~moacetyl-['~C] isonipecotic acid (Lp) via the corresponding diazoketone, followed by intamolecular cyclization, gave the key intermediate 3-q~inuclidone-[3-'~C] (a). 3-quin~clidone-[3-'~C] was converted to a mixture of phenethylamine diastereomers.

Carrier free crystallization and hydrogenolysis furnished both (R) and (S) 3-aminoquin~clidine-[3-'~C] enantiomers at >99% optical purity.

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