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【结 构 式】

【分子编号】63103

【品名】1-[(4R)-4-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone

【CA登记号】

【 分 子 式 】C21H25NO5

【 分 子 量 】371.43324

【元素组成】C 67.91% H 6.78% N 3.77% O 21.54%

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:(VII)

Amino alcohol (III) was prepared from veratraldehyde (I) by addition of cyanotrimethylsilane, followed by borane reduction of the resultant cyanohydrin (II). Reductive condensation of amine (III) with 2,3-dimethoxybenzaldehyde (IV) gave the secondary amine (V). This was cyclized to the tetrahydroisoquinoline (VI) under acidic conditions. Resolution of the racemic (VI) by means of dibenzoyltartaric acid furnished the desired (S)-amine, which was further acylated with Ac2O to yield the chiral amide (VII). Demethylation of (VII) with boron tribromide afforded the tetrahydroxy compound (VIII). Finally, acetamide hydrolysis under acidic conditions yielded the title compound.

1 Anan, H.; Tanaka, A.; Tsuzuki, R.; Yokota, M.; Yatsu, T.; Honda, K.; Asano, M.; Fujita, S.; Furuya, T.; Fujikura, T.; Synthesis, resolution, and renal vasodilation activity of novel DA1 agonists: 4-(3,4-Dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline derivatives. Chem Pharm Bull 1991, 39, 11, 2910.
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) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 63099 2-(3,4-dimethoxyphenyl)-2-[(trimethylsilyl)oxy]acetonitrile C13H19NO3Si 详情 详情
(III) 63100 2-amino-1-(3,4-dimethoxyphenyl)-1-ethanol C10H15NO3 详情 详情
(IV) 17615 2,3-Dimethoxybenzaldehyde 86-51-1 C9H10O3 详情 详情
(V) 63101 2-[(2,3-dimethoxybenzyl)amino]-1-(3,4-dimethoxyphenyl)-1-ethanol C19H25NO5 详情 详情
(VI) 63102 4-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 4-(3,4-dimethoxyphenyl)-7-methoxy-1,2,3,4-tetrahydro-8-isoquinolinyl methyl ether C19H23NO4 详情 详情
(VII) 63103 1-[(4R)-4-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone C21H25NO5 详情 详情
(VIII) 63104 1-[(4R)-4-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone C17H17NO5 详情 详情
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