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【结 构 式】 
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【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% |
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 |