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Synthesis of specifically labeled (S)-nicotine-5-3H and (S)-cotinine-5-3H BY carrier free tritiolysis of the corresponding 5-bromo derivatives

✍ Scribed by Mark K. Shigenaga; Peyton Jacob; Anthony Trevor; Neal Castagnoli Jr.; Neal Benowitz

Publisher: John Wiley and Sons
Year: 1987
Tongue: French
Weight: 499 KB
Volume: 24
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580240614

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✦ Synopsis

The synthesis of high specific activity tritium labeled (S)-nicotine and (S)-cotinine has been achieved. ( S ) - 5-Bromonornicotine of high enantiomeric purity was converted to the corresponding (S) -5-bromonicotine by reductive amination with formaldehyde and sodium borohydride.

Tritidysis of this intermediate with carrier free tritium in the presence of triethylamine using 10% PdfG catalyst provided (S)-nicotine-5-H with a specific activity of 32 Cifmmol in ethanol solvent and 28 Ci/mmol in tetrahydrofuran solvent. Similarly, tritiation of (S)-5-bromocotinine, obtained by oxidation of (S)-5bromonicotine with bromine followed by reduction of the intermediate (S)-3',3',5-tribromonicotine with zinc dust, yielded the corresponding (S)-cotinine-5-H (22.8 Cifmmol).

All reactions proceeded in good to excellent yields.

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