Pipecuronium bromide, RGH-1106, Arduan
哌库溴铵 Chemical Name: 2beta,16beta-Bis(4',4'-dimethylpiperazino)-3alpha,17beta-diacetoxy-5alpha-androstane dibromide dihydrate; 4,4'-(3,17-Diacetoxyandrostane-2,16-diyl)-bis(1,1-dimethylpiperazinium)dibromide dihydrate; 4,4'-(3alpha,17beta-Dihydroxy-5alpha-androstan-2beta,16beta-ylene)bis[1,1-dimethylpiperazinium]dibromide diacetate (ester) dihydrate; 4,4'-[(2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl]bis[1,1-dimethylpiperazinium]dibromide dihydrate
CAS No. 68399-57-5, 52212-02-9 (anhydrous)
项目整合开发状态: Withdrawn
项目研究机构: Gedeon Richter (Originator), Organon (Originator)
合成路线:The reaction of 5alpha-androst-2-ene-17-one (I) with isopropenyl acetate (II) by means of H2SO4 as catalyst gives 17beta-acetoxy-5alpha-androsta-2,16-diene (III),which is epoxidized by means of perbenzoic acid (A) in benezene yielding 2alpha,3alpha:16alpha,17alpha-diepoxy-17beta-acetoxy-5alpha-androstane (IV).The reaction of (IV) with N-methylpiperazine (V) in refluxing water affords 2beta,16beta-bis(4-methyl-1-piperazino)-3alpha-hydroxy-5alpha-androstane-17-one (VI),which is reduced with NaBH4 in THF methanol to give 2,16-bis(4-methyl-1-piperazino)-3alpha,17beta-dihydroxy-5alpha-androstane (VII).The acetylation of (VII) with acetic anhydride by means of ZnCl2 in acetic acid yields 2beta,16beta-bis(4-methyl-1-piperazino)-3alpha,17beta-diacetoxy-5alpha-androstane (VIII),which is finally treated with methyl bromide in acetone.
📌 参考资料/链接：
参考文献标题:
文献作者:Tuba,Z.; et al.
参考来源:GB 1398050
📄 详细内容
合成路线:The reaction of 5alpha-androst-2-ene-17-one (I) with isopropenyl acetate (II) by means of H2SO4 as catalyst gives 17beta-acetoxy-5alpha-androsta-2,16-diene (III),which is epoxidized by means of perbenzoic acid (A) in benezene yielding 2alpha,3alpha:16alpha,17alpha-diepoxy-17beta-acetoxy-5alpha-androstane (IV).The reaction of (IV) with N-methylpiperazine (V) in refluxing water affords 2beta,16beta-bis(4-methyl-1-piperazino)-3alpha-hydroxy-5alpha-androstane-17-one (VI),which is reduced with NaBH4 in THF methanol to give 2,16-bis(4-methyl-1-piperazino)-3alpha,17beta-dihydroxy-5alpha-androstane (VII).The acetylation of (VII) with acetic anhydride by means of ZnCl2 in acetic acid yields 2beta,16beta-bis(4-methyl-1-piperazino)-3alpha,17beta-diacetoxy-5alpha-androstane (VIII),which is finally treated with methyl bromide in acetone.
参考文献标题:
文献作者:
参考来源:US 312398
合成路线:The reaction of 5alpha-androst-2-ene-17-one (I) with isopropenyl acetate (II) by means of H2SO4 as catalyst gives 17beta-acetoxy-5alpha-androsta-2,16-diene (III),which is epoxidized by means of perbenzoic acid (A) in benezene yielding 2alpha,3alpha:16alpha,17alpha-diepoxy-17beta-acetoxy-5alpha-androstane (IV).The reaction of (IV) with N-methylpiperazine (V) in refluxing water affords 2beta,16beta-bis(4-methyl-1-piperazino)-3alpha-hydroxy-5alpha-androstane-17-one (VI),which is reduced with NaBH4 in THF methanol to give 2,16-bis(4-methyl-1-piperazino)-3alpha,17beta-dihydroxy-5alpha-androstane (VII).The acetylation of (VII) with acetic anhydride by means of ZnCl2 in acetic acid yields 2beta,16beta-bis(4-methyl-1-piperazino)-3alpha,17beta-diacetoxy-5alpha-androstane (VIII),which is finally treated with methyl bromide in acetone.
参考文献标题:Pipecuronium bromide
文献作者:Blancafort,P.; Castar,J.; Serradell,M.N.; Hopkins,S.J.
参考来源:Drugs Fut 1980,5(12),621
产品链接: CAS No. 68399-57-5›› 产品链接: CAS No.52212-02-9››