Synthesis of the carbon-14 labeled isotopomers of(R)-N-methyl-3-[2-methylphenoxyl]-benzenepropanamine hydrochloride(atomoxetine hydrochloride, LY139603), and two of its metabolites
| Autor: | William J. Wheeler, Dean K. Clodfelter, Fengjiun Kuo |
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| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Ketone Hydrochloride Organic Chemistry Biochemistry Chemical synthesis Analytical Chemistry Stille reaction Isotopomers chemistry.chemical_compound chemistry Reagent Drug Discovery Organic chemistry Radiology Nuclear Medicine and imaging Mitsunobu reaction Spectroscopy Atomoxetine hydrochloride |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 47:615-625 |
| ISSN: | 1099-1344 0362-4803 |
| Popis: | Carbon-14 labeled StraterraTM (Atomoxetine HCl, LY139603, (-)-N-methyl-3-(2-methylphenoxy)-benzenepropanamine hydrochloride), a potent inhibitor of the presynaptic norepinephrine transporter, and two of its major metabolites were synthesized. The key component, S-(+)-3-chloro-l-phenyl-l-propanol-[1-14C] was synthesized by Stille coupling of benzoyl chloride-[carbonyl-14C] with vinyl tri-n-butylstannane, followed by HCl addition to the vinyl ketone, and asymmetric reduction of the ketone by Corey's CBS reagent. Mitsunobu reaction of this S-(+)-3-chloro-l-phenyl-l-propanol-[1-14C] with various phenol derivatives, followed by converting the chloride to amines, gave desired products. Copyright © 2004 John Wiley & Sons, Ltd. |
| Databáze: | OpenAIRE |
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