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【结 构 式】 
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【分子编号】29059 【品名】N-[(4aR,5R,8aS)-2-methyldecahydro-5-isoquinolinyl]acetamide 【CA登记号】 |
【 分 子 式 】C12H22N2O 【 分 子 量 】210.31956 【元素组成】C 68.53% H 10.54% N 13.32% O 7.61% |
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 reduction of 5-nitro-2-methylisoquinolinium p-toluenesulfonate (I) with H2 over PtO2 in acetic acid H2SO4 gives 5-amino-2-methyldecahydroisoquinoline (II), which is acetylated with acetic anhydride in DMF and submitted to fractionated crystallization to give trans-5,9,10-H-5-acetamido-2-methyldecahydroisoquinoline (III). Hydrolysis of (III) with H2SO4 in refluxing water yields trans-5,9,10-H-5-amino-2-methylisoquinoline (IV), which is finally acylated with 3,4,5-trimethoxybenzoyl chloride (V) by means of KHCO3 in benzene.
| 【1】 Peters, E.R.; Marthinson, I.W.; Fowler, S.J.; Lawson, J.W.; Gueldner, R.C.; The stereochemistry of 5-substituted decahydroisoquinolines and their antiarrhythmic activity. J Med Chem 1968, 11, 5, 997. |
| 【2】 Mathison, I.W. (Aventis Pharmaceuticals, Inc.); Benzamido 2 lower alkyl decahydroisoquinolines. DE 1900948; FR 2004748; GB 1246051; JP 7114060; US 3674791 . |
| 【3】 Sneddon, J.; Serradell, M.N.; Castaner, J.; M-30 and M-32. Drugs Fut 1985, 10, 3, 203. |
| 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) | 29055 | 2-methyl-5-nitroisoquinolinium phenylmethanesulfonate | C17H16N2O5S | 详情 | 详情 | |
| (II) | 29056 | 2-methyldecahydro-5-isoquinolinamine | C10H20N2 | 详情 | 详情 | |
| (III) | 29059 | N-[(4aR,5R,8aS)-2-methyldecahydro-5-isoquinolinyl]acetamide | C12H22N2O | 详情 | 详情 | |
| (IV) | 29060 | (4aR,5R,8aS)-2-methyldecahydro-5-isoquinolinamine | C10H20N2 | 详情 | 详情 | |
| (V) | 13571 | 3,4,5Ttrimethoxybenzoyl chloride | 4521-61-3 | C10H11ClO4 | 详情 | 详情 |
Extended Information