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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
- Source :
- Journal of Labelled Compounds and Radiopharmaceuticals. 24:713-723
- Publication Year :
- 1987
- Publisher :
- Wiley, 1987.
-
Abstract
- 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. Tritiolysis of this intermediate with carrier free tritium in the presence of triethylamine using 10% Pd/C catalyst provided (S)-nicotine-5- H with a specific activity of 32 Ci/mmol in ethanol solvent and 28 Ci/mmol in tetrahydrofuran solvent. Similarly, tritiation of (S)-5-bromocotinine, obtained by oxidation of (S)-5-bromocotinine, obtained by oxidation of (S)-5-bromonicotine 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 Ci/mmol). All reactions proceeded in good to excellent yields.
- Subjects :
- Bromine
Organic Chemistry
Formaldehyde
chemistry.chemical_element
Biochemistry
Medicinal chemistry
Reductive amination
Analytical Chemistry
Solvent
chemistry.chemical_compound
Sodium borohydride
chemistry
Drug Discovery
Organic chemistry
Radiology, Nuclear Medicine and imaging
Tritium
Triethylamine
Spectroscopy
Tetrahydrofuran
Subjects
Details
- ISSN :
- 03624803
- Volume :
- 24
- Database :
- OpenAIRE
- Journal :
- Journal of Labelled Compounds and Radiopharmaceuticals
- Accession number :
- edsair.doi...........d0827a03e9f881b344fa80d9dacabd87