Vecuronium bromide, Org-NC-45, Norcuron
维库溴铵Chemical Name: 1-[(2beta,3alpha,5alpha,16beta,17beta)-3,17-Diacetoxy-2-(1-piperidinyl)androstan-16-yl]-1-methylpiperidinium bromide; 3alpha,17beta-Diacetoxy-2beta,16beta-bis(1-piperidino)androstane 16-monomethobromide; 1-[(2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)-2-(1-piperidinyl)androstan-16-yl]-1-methylpiperidinium bromide
CAS No. 50700-72-6
项目整合开发状态: Launched-1982
项目研究机构: Organon (Originator)
合成路线:The enol acylation of 5alpha-androst-2-en-17-one (I) with isopropenyl acetate (A) using H2SO4 as catalyst gives 17-acetoxyandrost-2,16-diene (II),which is epoxidized by treatment with m-chloroperbenzoic acid in ether yielding 2alpha,3alpha:16alpha,17alpha-diepoxy-17beta-acetoxy-5alpha-androstane (III).The hydrolytic rearrangement of (III) with KOH affords 2alpha,3alpha-epoxy-5alpha-androstan-17beta-ol-16-one (IV),which is condensed with refluxing aqueous piperidine (B) to give 2beta,16beta-dipiperidino-5alpha-androstan-3alpha-ol-17-one (V).The reduction of (V) with NaBH4 in methylene chloride - methanol yields 2beta,16beta-dipiperidino-5alpha-androstan-3alpha,17beta-diol (VI),which is acetylated by reaction with acetyl chloride as usual to afford the corresponding diacetate (VII).Finally,this compound is quaternized by reaction with methyl bromide in ether.
📌 参考资料/链接：
参考文献标题:ORG-NC-45
文献作者:Serradell,M.N.; Castar,J.; Blancafort,P.; Hillier,K.
参考来源:Drugs Fut 1981,6(5),287
📄 详细内容
合成路线:The enol acylation of 5alpha-androst-2-en-17-one (I) with isopropenyl acetate (A) using H2SO4 as catalyst gives 17-acetoxyandrost-2,16-diene (II),which is epoxidized by treatment with m-chloroperbenzoic acid in ether yielding 2alpha,3alpha:16alpha,17alpha-diepoxy-17beta-acetoxy-5alpha-androstane (III).The hydrolytic rearrangement of (III) with KOH affords 2alpha,3alpha-epoxy-5alpha-androstan-17beta-ol-16-one (IV),which is condensed with refluxing aqueous piperidine (B) to give 2beta,16beta-dipiperidino-5alpha-androstan-3alpha-ol-17-one (V).The reduction of (V) with NaBH4 in methylene chloride - methanol yields 2beta,16beta-dipiperidino-5alpha-androstan-3alpha,17beta-diol (VI),which is acetylated by reaction with acetyl chloride as usual to afford the corresponding diacetate (VII).Finally,this compound is quaternized by reaction with methyl bromide in ether.
参考文献标题:Pancuronium bromide and other steroidal neuromuscular blocking agents containing acetylcholine fragments
文献作者:Buckett,W.R.; Hewett,C.L.; Savage,D.S.
参考来源:J Med Chem 1973,16(10),1116-24
产品链接: CAS No. 50700-72-6››