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【结 构 式】 
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【分子编号】40608 【品名】(4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-ol 【CA登记号】 |
【 分 子 式 】C13H18N2O2 【 分 子 量 】234.2982 【元素组成】C 66.64% H 7.74% N 11.96% O 13.66% |
合成路线1
该中间体在本合成路线中的序号：(III)The oxidation of eserine (I) by means of H2O2 and KHCO3 produced the geneseroline carbamate (II), which was hydrolyzed to geneseroline (III) employing 62% sulfuric acid at 85 C. The desired carbamate was then obtained by condensation of (III) with 2-ethylphenyl isocyanate (IV) either in the presence of K2CO3 in acetone or in the presence of t-BuOK under sonication, and the title compound was then isolated as the corresponding hydrochloride salt.
| 【1】 Ventura, P.; Pighi, R.; Servadio, V.; Pietra, C.; Amari, G.; Salsi, B.; Pivetti, F.; Delcanale, M.; Chiesi, P.; Villetti, G. (Chiesi Farmaceutici SpA); A process for the preparation of aminocarbonyl derivs. of geneseroline having selective brain anticholinesterase activity. WO 9919329 . |
| 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) | 40606 | (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate | 57-47-6 | C15H21N3O2 | 详情 | 详情 |
| (II) | 40607 | (4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-yl methylcarbamate | C15H21N3O3 | 详情 | 详情 | |
| (III) | 40608 | (4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-ol | C13H18N2O2 | 详情 | 详情 | |
| (IV) | 40609 | 2-ethylphenyl isocyanate; 1-ethyl-2-isocyanatobenzene | 40411-25-4 | C9H9NO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)An alternative procedure for the preparation of the intermediate geneseroline (III) consisted in the oxidation of eseretole (V) to geneseretole (VI), followed by ether cleavage by means of concentrated sulfuric acid.
| 【1】 Ventura, P.; Pighi, R.; Servadio, V.; Pietra, C.; Amari, G.; Salsi, B.; Pivetti, F.; Delcanale, M.; Chiesi, P.; Villetti, G. (Chiesi Farmaceutici SpA); A process for the preparation of aminocarbonyl derivs. of geneseroline having selective brain anticholinesterase activity. WO 9919329 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 40608 | (4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-ol | C13H18N2O2 | 详情 | 详情 | |
| (V) | 40610 | (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ethyl ether; (3aS,8aR)-5-ethoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole | C15H22N2O | 详情 | 详情 | |
| (VI) | 40611 | (4aS,9aS)-6-ethoxy-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indole; (4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-yl ethyl ether | C15H22N2O2 | 详情 | 详情 |