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【结 构 式】

【分子编号】41230

【品名】(4aS,6R,8aS)-6-hydroxy-11-methyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-3-yl methylcarbamate

【CA登记号】

【 分 子 式 】C18H22N2O4

【 分 子 量 】330.38376

【元素组成】C 65.44% H 6.71% N 8.48% O 19.37%

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:(III)

The demethylation of galanthamine (I) with ethyl mercaptane sodium salt in hot DMF gives 6-demethylgalanthamine (II), which is selectively monoesterified at the phenolic OH with N-methylcarbamic acid and CDI yielding the monoester (III). Finally this compound is esterified again at the remaining OH with isobutyric anhydride (IV) and TEA or DMAP affording the target diester. The selective monoesterification of (II) can also be performed with N-methylcarbamic anhydride and TEA or DMAP, with N-methylcarbamoyl chloride and DBU, or with N-methylisocyanate and K2CO3.

1 Bores, G.M.; Kosley, R.W. Jr.; Galanthamine derivatives for the treatment of Alzeimer's disease. Drugs Fut 1996, 21, 6, 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) 39110 Sodium 1-ethanethiolate; Sodium ethylmercaptide 811-51-8 C2H5NaS 详情 详情
(I) 41226 (4aS,6R,8aS)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol 357-70-0 C17H21NO3 详情 详情
(II) 41227 (4aS,6R,8aS)-11-methyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol C16H19NO3 详情 详情
(III) 41230 (4aS,6R,8aS)-6-hydroxy-11-methyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-3-yl methylcarbamate C18H22N2O4 详情 详情
(IV) 22334 1-methylpropionic anhydride 97-72-3 C8H14O3 详情 详情
Extended Information