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【结 构 式】

【分子编号】39217

【品名】(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-10,13-dimethyl-2,16-bis(4-methyl-1-piperazinyl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol

【CA登记号】

【 分 子 式 】C29H52N4O2

【 分 子 量 】488.75764

【元素组成】C 71.27% H 10.72% N 11.46% O 6.55%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

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.

1 US 312398 .
2 Tuba, Z.; et al.; GB 1398050 .
3 Blancafort, P.; Castaner, J.; Serradell, M.N.; Hopkins, S.J.; Pipecuronium bromide. Drugs Fut 1980, 5, 12, 621.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 39215 benzenecarboperoxoic acid 93-59-4 C7H6O3 详情 详情
(I) 32178 (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-1,4,5,6,7,8,9,10,11,12,13,14,15,16-tetradecahydro-17H-cyclopenta[a]phenanthren-17-one C19H28O 详情 详情
(II) 21178 isopropenyl acetate 108-22-5 C5H8O2 详情 详情
(III) 32179 (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate C21H30O2 详情 详情
(IV) 13647 (1aR,2aS,2bS,4aS,5aR,6aS,6bR,8aS,9aS)-2a,4a-dimethylhexadecahydro-4bH-oxireno[2'',3'':4',5']cyclopenta[1',2':7,8]phenanthro[2,3-b]oxiren-4-yl acetate C21H30O4 详情 详情
(V) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(VI) 39216 (2S,3S,5S,8R,9S,10S,13S,14S,16S)-3-hydroxy-10,13-dimethyl-2,16-bis(4-methyl-1-piperazinyl)hexadecahydro-17H-cyclopenta[a]phenanthren-17-one C29H50N4O2 详情 详情
(VII) 39217 (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-10,13-dimethyl-2,16-bis(4-methyl-1-piperazinyl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol C29H52N4O2 详情 详情
(VIII) 39218 (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-(acetoxy)-10,13-dimethyl-2,16-bis(4-methyl-1-piperazinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C33H56N4O4 详情 详情
Extended Information