Synthese d'un nouvel anorexigene marque au 14C : le (Trifluoromethylthio-3′ phenyl)-1 Ethylamino-2 Propane 14C-1

✍ Scribed by L. Pichat; J. Tostain

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: French
• Weight: 363 KB
• Volume: 16
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580160203

✦ Synopsis

Carbonatation o f 3-trifluoromethylthio phenylmagnesiwn bromide 2 w i t h 14C02 leads t o (carboxyl-14C) 3-trifluoromethylthio benzofc acid 3 . Reduction of t h e l a t t e r w i t h borane-methyl s u l f i d e compZex (CH312S-BH3 i n presence of trimethyl borate gives r i s e t o 3-trifluoromethylthio benzyl alcohol 4 , which i s oridized by lead t e t r a c e t a t e i n pyridine t o give 3-trifluorornethylthio benzaldehyde 14CO methylthio phenyl)-2-nitropropene-l-14C reduced by Fe-HCl i n presence o f FeC13 i n t o 1-(3'-trifluoromethyZt h i o phenyll-2-propanone-I-14C

7 . Condensation o f ethylamine w i t h the ketone followed by reduction i n s i t u w i t h sodiwn borohydride leads t o 2-(3t-trifluoromethylthio phenyl)-2-ethylwrtino propane-l-14C8 i s o l a t e d as the hydrochloride. S p e c i f i c a c t i v i t y

: 47 mCi/mMole w i t h an overall y i e l d o f 10 % based on barium carbonate-14C.