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【结 构 式】 
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【分子编号】49438 【品名】methyl 5,6-dimethoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalenylcarbamate 【CA登记号】 |
【 分 子 式 】C14H17NO5 【 分 子 量 】279.29272 【元素组成】C 60.21% H 6.14% N 5.02% O 28.64% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)Condensation of 4-(2,3-dimethoxyphenyl)-2-oxo-3-butenoic acid (VIII) with methyl carbamate (XV) by means of TsOH in refluxing toluene gives the substituted furanone (XVI), which is hydrogenated with H2 over Pd/C in hot ethanol to yield 4-(2,3-dimethoxyphenyl)-2-(methoxycarbonylamino)butyric acid (XVII). Cyclization of acid (XVII) by means of PPA at 60 C affords tetralone (XVIII), which is reduced with H2 over Pd/C in an autoclave at 80 C to provide N-(5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)carbamic acid methyl ester (XIX). Finally, the carbamoyl group of (XIX) is reduced with LiAlH4 in hot THF to yield N-(5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N-methylamine (V).
| 【1】 Castaner, J.; Mealy, N.E.; Bayes, M.; Leeson, P.A.; Nolomirole Hydrochloride. Drugs Fut 2001, 26, 11, 1046. |
| 【2】 Servadio, V.; Ventura, P.; Amari, G.; Chiesi, P.; Del Canale, M.; De Fanti, R. (Chiesi Farmaceutici SpA); A process for the preparation of 5,6-dihydroxy-2-amino-1,2,3,4-tetrahydronaphthalene derivs.. WO 9529147 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 37381 | N-(5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-N-methylamine; 5,6-dimethoxy-N-methyl-1,2,3,4-tetrahydro-2-naphthalenamine | C13H19NO2 | 详情 | 详情 | |
| (VIII) | 37376 | (E)-4-(2,3-dimethoxyphenyl)-2-oxo-3-butenoic acid | C12H12O5 | 详情 | 详情 | |
| (XV) | 40724 | methyl carbamate; carbamic acid methyl ester | 598-55-0 | C2H5NO2 | 详情 | 详情 |
| (XVI) | 49436 | methyl 5-(2,3-dimethoxyphenyl)-2-oxo-2,5-dihydro-3-furanylcarbamate | C14H15NO6 | 详情 | 详情 | |
| (XVII) | 49437 | 4-(2,3-dimethoxyphenyl)-2-[(methoxycarbonyl)amino]butyric acid | C14H19NO6 | 详情 | 详情 | |
| (XVIII) | 49438 | methyl 5,6-dimethoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalenylcarbamate | C14H17NO5 | 详情 | 详情 | |
| (XIX) | 49439 | methyl 5,6-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenylcarbamate | C14H19NO4 | 详情 | 详情 |