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【结 构 式】

【分子编号】29058

【品名】(4aS,5R,8aS)-2-methyldecahydro-5-isoquinolinamine

【CA登记号】

【 分 子 式 】C10H20N2

【 分 子 量 】168.28228

【元素组成】C 71.37% H 11.98% N 16.65%

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:(IV)

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 cis-5,9,10-H-5-acetamido-2-methyldecahydroisoquinoline (III). Hydrolysis of (III) with H2SO4 in refluxing water yields cis-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.; M-30 and M-32. Drugs Fut 1985, 10, 3, 202.
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) 29057 N-[(4aS,5R,8aS)-2-methyldecahydro-5-isoquinolinyl]acetamide C12H22N2O 详情 详情
(IV) 29058 (4aS,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