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【结 构 式】 
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【分子编号】44051 【品名】4-[2-bromo-1-(tert-butoxy)ethyl]phenyl methyl ether; 1-[2-bromo-1-(tert-butoxy)ethyl]-4-methoxybenzene 【CA登记号】 |
【 分 子 式 】C13H19BrO2 【 分 子 量 】287.19666 【元素组成】C 54.37% H 6.67% Br 27.82% O 11.14% |
合成路线1
该中间体在本合成路线中的序号：(III)The bromination of 4-methoxystyrene (I) with Br2 gives the alpha,beta-dibromo derivative (II), which by selective debromination with potassium tert-butoxide yields the tert-butyl ether (III). The condensation of (III) with 2-(2-chloro-3,4-dimethoxyphenyl)ethylamine (IV) affords the secondary amine (V), which is deprotected with H2SO4 to provide the substituted ethanolamine (VI). The cyclization of (VI) by means of Ms-OH and trifluoroacetic acid gives the 3-benzazepine (VII), which is finally demethylated with BBr3 and treated with methanesulfonic acid to afford the target mesylate.
| 【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645. |
| 【2】 US 4321195 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 44049 | 1-methoxy-4-vinylbenzene; methyl 4-vinylphenyl ether | 637-69-4 | C9H10O | 详情 | 详情 |
| (II) | 44050 | 4-(1,2-dibromoethyl)phenyl methyl ether; 1-(1,2-dibromoethyl)-4-methoxybenzene | C9H10Br2O | 详情 | 详情 | |
| (III) | 44051 | 4-[2-bromo-1-(tert-butoxy)ethyl]phenyl methyl ether; 1-[2-bromo-1-(tert-butoxy)ethyl]-4-methoxybenzene | C13H19BrO2 | 详情 | 详情 | |
| (IV) | 42037 | 2-chloro-3,4-dimethoxyphenethylamine; 2-(2-chloro-3,4-dimethoxyphenyl)-1-ethanamine | 67287-36-9 | C10H14ClNO2 | 详情 | 详情 |
| (V) | 44052 | 2-(tert-butoxy)-N-(2-chloro-3,4-dimethoxyphenethyl)-2-(4-methoxyphenyl)-1-ethanamine; N-[2-(tert-butoxy)-2-(4-methoxyphenyl)ethyl]-N-(2-chloro-3,4-dimethoxyphenethyl)amine | C23H32ClNO4 | 详情 | 详情 | |
| (VI) | 31702 | 2-[(2-chloro-3,4-dimethoxyphenethyl)amino]-1-(4-methoxyphenyl)-1-ethanol | C19H24ClNO4 | 详情 | 详情 | |
| (VII) | 31704 | 4-(6-chloro-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl)phenyl methyl ether; 6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine | C19H22ClNO3 | 详情 | 详情 |