✦ LIBER ✦

Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part II

✍ Scribed by Mohammad R. Masjedizadeh; Howard Parnes

Publisher: John Wiley and Sons
Year: 1996
Tongue: French
Weight: 398 KB
Volume: 38
Category: Article
ISSN: 0022-2135
DOI: 10.1002/(sici)1099-1344(199601)38:1<53::aid-jlcr812>3.0.co;2-f

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✦ Synopsis

S)-3-Aminoquinuclidine-3H 1 Oc-S having a specific activity of 66 Ci/mrnol was prepared in eight steps from lsonicotinic acid (2). Reduction of 2 with carrier free tritium gas over PtO2 In DMF gave isonipecotic acid-3H &.

Conversion to a-bromo ketone followed by cyclization afforded 3-quinuclidone-3H &. Racemic 3-aminoquinuclidine-3H & was prepared by conversion of & to oxime LE followed by reduction with NaBHdNiC12*6H20.

Racemic & was resolved with (R)-methylbenzyl isocyanate.

Hydrolysis of Sc-S.s afforded (S~-3-aminoquinuclidine-3H 1Oc-S. The enantiopurity was >99.5% (S).

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