(4aS,5R,8aS)-2-methyldecahydro-5-isoquinolinamine -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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