Org-6370
Chemical Name: dl-11-anti-Dimethylaminebenzo[b]bicyclo[3.3.1]nona-3,6a(10a)-diene hydrochloride; dl-(5alpha,9alpha,11S*)-5,6,9,10-Tetrahydro-N,N-dimethyl-5,9-methanobenzocycloocten-11-amine hydrochloride
CAS No. 94725-41-4
项目整合开发状态: Phase II
项目研究机构: Akzo Nobel (Originator)
合成路线:The synthesis of Org-6370 is carried out in eight steps as follows:The 5,9-methanobenzocyclooctene system is prepared from tetralonepyrrolidine enamine (I) and acrolein (II),giving a mixture of the epimeric 8-alcohols (III),which are dehydroxylated via the intermediate p-toluenesulfonate esters.The unsaturated 11-ketone (IV) is converted by a reductive amination process using methylamine and sodium borohydride to an epimeric mixture of 11-methylamines.At this stage the epimeric amines are separated by crystallization and the required (11S*)-compound (V) is further methylated and converted to the hydrochloride.
📌 参考资料/链接：
参考文献标题:ORG-6370
文献作者:Pento,J.T.
参考来源:Drugs Fut 1989,14(2),130
📄 详细内容
合成路线:The synthesis of Org-6370 is carried out in eight steps as follows:The 5,9-methanobenzocyclooctene system is prepared from tetralonepyrrolidine enamine (I) and acrolein (II),giving a mixture of the epimeric 8-alcohols (III),which are dehydroxylated via the intermediate p-toluenesulfonate esters.The unsaturated 11-ketone (IV) is converted by a reductive amination process using methylamine and sodium borohydride to an epimeric mixture of 11-methylamines.At this stage the epimeric amines are separated by crystallization and the required (11S*)-compound (V) is further methylated and converted to the hydrochloride.
参考文献标题:ORG-6370
文献作者:Timmer,C.J.; van der Waart,M.; Sam,A.P.; Sitsen,J.M.A.; de Graaf,J.S.; Redpath,J.
参考来源:London: Libbey (B.S.Meldrum and R.J.Porter (Eds.) 1986,