RWJ-52807
Chemical Name: (3aR,10cR)-2-Methyl-1,2,3,3a,4,5,6,10c-octahydropyrrolo[3,4-c]carbazole
项目整合开发状态: Preclinical
项目研究机构: R.W. Johnson (Originator)
合成路线:The condensation of phenyl hydrazine (I) with the cis N-methyl-perhydroisoindoletrione (II) gave hydrazone (III),which underwent Fischer indole synthesis upon treatment with methanolic H2SO4 to afford the pyrrolocarbazole (IV) as the major regioisomer (1).Reduction of the imide group of (IV) with aluminum hydride,generated from LiAlH4 and H2SO4,provided the corresponding amine as a racemic mixture.Separation of the desired (R,R)-enantiomer was then achieved by chiral HPLC on Chiralcel(R) OJ.
📌 参考资料/链接：
参考文献标题:Octahydropyrrolo-[3,4-c]carbazoles useful as analgesic agents
文献作者:Pitis,P.M.; Carmosin,R.J.; Carson,J.R.(Ortho-McNeil Pharmaceutical,Inc.)
参考来源:US 6063803; WO 9965911
📄 详细内容
合成路线:The condensation of phenyl hydrazine (I) with the cis N-methyl-perhydroisoindoletrione (II) gave hydrazone (III),which underwent Fischer indole synthesis upon treatment with methanolic H2SO4 to afford the pyrrolocarbazole (IV) as the major regioisomer (1).Reduction of the imide group of (IV) with aluminum hydride,generated from LiAlH4 and H2SO4,provided the corresponding amine as a racemic mixture.Separation of the desired (R,R)-enantiomer was then achieved by chiral HPLC on Chiralcel(R) OJ.
参考文献标题:
文献作者:Berman,B.; Kaufman,J.
参考来源:Can J Chem 1982,60(4),419-424