U-50488 hydrochloride
Chemical Name: trans-2-(3,4-Dichlorophenyl)-N-methyl-N-(2-pyrrolidinocyclohexyl)acetamide hydrochloride
CAS No. 67197-96-0, 67198-13-4 (free base)
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:The condensation of cyclohexene-epoxide (I) with pyrrolidine (II) gives trans-2-(1-pyrrolidinyl)cyclohexanol (III),which by reaction with NaH and methanesulfonyl chloride,and then with benzylamine is converted into trans-2-(1-pyrrolidinyl)-N-benzylcyclohexylamine (IV).The debenzylation of (IV) by hydrogenolysis with H2 over Pd/C affords trans-2-(1-pyrrolidinyl)cyclohexylamine (V),which is formylated with ethyl formate to the corresponding N-formyl-trans-2-(1-pyrrolidinyl)cyclohexylamine (VI).The reduction of (VI) with LiAlH4 in refluxing ether gives trans-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine (VII),which is finally condensed with 3,4-dichlorophenylacetic acid (VIII) by means of carbonyl diimidazole (IX) in THF.
📌 参考资料/链接：
参考文献标题:2-Aminocycloaliphatic amide compounds
文献作者:Szmuszkovicz,J.
参考来源:DE 2749950; ES 463876; FR 2370723; GB 1569225; JP 53063351; JP 61233654; US 4145435
📄 详细内容
合成路线:The condensation of cyclohexene-epoxide (I) with pyrrolidine (II) gives trans-2-(1-pyrrolidinyl)cyclohexanol (III),which by reaction with NaH and methanesulfonyl chloride,and then with benzylamine is converted into trans-2-(1-pyrrolidinyl)-N-benzylcyclohexylamine (IV).The debenzylation of (IV) by hydrogenolysis with H2 over Pd/C affords trans-2-(1-pyrrolidinyl)cyclohexylamine (V),which is formylated with ethyl formate to the corresponding N-formyl-trans-2-(1-pyrrolidinyl)cyclohexylamine (VI).The reduction of (VI) with LiAlH4 in refluxing ether gives trans-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine (VII),which is finally condensed with 3,4-dichlorophenylacetic acid (VIII) by means of carbonyl diimidazole (IX) in THF.
参考文献标题:U-50488
文献作者:Blancafort,P.; Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1982,7(6),416
产品链接: CAS No. 67197-96-0›› 产品链接: CAS No.67198-13-4››