(S)-PD-148903
6-(二丙基氨基)-3,4,5,6,7,8-六氢萘-1(2H)-酮 Chemical Name: (-)-6(S)-(Dipropylamino)-1,2,3,4,5,6,7,8-octahydronaphthalen-1-one hydrochloride
CAS No. 335158-94-6, 256474-06-3 (undefined isomer, free base)
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:Mannich reaction of 1,3-cyclohexanedione (I) with paraformaldehyde and dipropylamine affords intermediate (II) which,without isolation is condensed with acetone under Robinson annulation conditions,to produce the bicyclic amino ketone (III).Enamine reduction in (III) using NaBH3CN in AcOH gives a racemic amine,which is resolved via formation of the corresponding diastereoisomeric salts with (-)-ditoluyltartaric acid,and finally isolated as the hydrochloride salt.
📌 参考资料/链接：
参考文献标题:Method for treating Parkinson's disease by administering (-)-5-keto-2-N,N-di-N-propylamino-tetrahydrotetralin
文献作者:Wise,L.D.; Wikstrom,H.V.; Wustrow,D.J.; Meltzer,L.T.; Dijkstra,D.; Venhuis,B.J.(Pfizer Inc.)
参考来源:WO 0128977
📄 详细内容
合成路线:Mannich reaction of 1,3-cyclohexanedione (I) with paraformaldehyde and dipropylamine affords intermediate (II) which,without isolation is condensed with acetone under Robinson annulation conditions,to produce the bicyclic amino ketone (III).Enamine reduction in (III) using NaBH3CN in AcOH gives a racemic amine,which is resolved via formation of the corresponding diastereoisomeric salts with (-)-ditoluyltartaric acid,and finally isolated as the hydrochloride salt.
参考文献标题:A new type of prodrug of catecholamines: An opportunity to improve the treatment of Parkinson's disease
文献作者:Venhuis,B.J.; Rodenhuis,N.; Wikstrom,H.V.; Wustrow,D.J.; Meltzer,L.T.; Wise,L.D.; Johnson,S.J.; Pugsley,T.A.; Sundell,S.; Dijkstra,D.
参考来源:J Med Chem 2002,45(12),2349
产品链接: CAS No.256474-06-3››