【药物名称】Pipecuronium bromide, RGH-1106, Arduan
化学结构式(Chemical Structure):
参考文献No.701435
标题:
作者:Tuba, Z.; et al.
来源:GB 1398050
合成路线图解说明:

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No.701436
标题:
作者:
来源:US 312398
合成路线图解说明:

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No.800505
标题:Pipecuronium bromide
作者:Blancafort, P.; Casta馿r, J.; Serradell, M.N.; Hopkins, S.J.
来源:Drugs Fut 1980,5(12),621
合成路线图解说明:

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.

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