✦ LIBER ✦

Synthesis of the carbon-14 labeled isotopomers of (R)-N-methyl-3-[2-methylphenoxyl]-benzenepropanamine hydrochloride (atomoxetine hydrochloride, LY139603), and two of its metabolites

✍ Scribed by Fengjiun Kuo; Dean K. Clodfelter; William J. Wheeler

Publisher: John Wiley and Sons
Year: 2004
Tongue: French
Weight: 125 KB
Volume: 47
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.849

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Carbon‐14 labeled Straterra^TM^ (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‐^14^C] was synthesized by Stille coupling of benzoyl chloride‐[carbonyl‐^14^C] 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‐^14^C] with various phenol derivatives, followed by converting the chloride to amines, gave desired products. Copyright © 2004 John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

The synthesis of (S)-di-n-propyl-(8-isox

The synthesis of (S)-di-n-propyl-(8-isoxazol-5-yl-1,2,3,4-tetrahydronaphthalen-2-yl)amine hydrochloride and its C-14-labeled isotopomer

✍ William J. Wheeler; Douglas D. O'Bannon; Steven Swanson; Todd A. Gillespie; Davi 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 French ⚖ 163 KB 👁 1 views

The partial ergoline LY228729 (1) which was a potent 5HT 1A agonist has been studied clinically. Somewhat later, a related analog, (S)-di-n-propyl-(8-isoxazol-5-yl-1,2,3,4-tetrahydronaphthalen-2-yl)amine (2a) which in addition to potent 5HT 1A agonist activity was a muscarinic antagonist, was chosen