|
【结 构 式】 
|
【分子编号】11146 【品名】(5aR,6aR,12bR)-7-Methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine 【CA登记号】 |
【 分 子 式 】C19H20N2 【 分 子 量 】276.38128 【元素组成】C 82.57% H 7.29% N 10.14% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenzo[c,d]indol-4-one (I) with methylamine followed by acylation of the resulting enamine with benzoyl chloride gives 1,N-dibenzoyl-4-(methylamino)-1,2,2a,3-tetrahydrobenzo[c,d]indole (II) which, by irradiation with UV light in acetone, is isomerized to (5aR*,6aS*,12bS*)-4-benzoyl-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridin-8-one (III). The reduction of (III) with LiAlH4 in ether, followed by hydrolysis with NaOH, and optical resolution with (+)-mandelic acid affords (+)-(5aS,6aR,12bR)-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine (IV), which is finally dehydrogenated with MnO2 in methylene chloride.
| 【1】 Hagenbach, A.; Seiler, M.P.; Wuthrich, H.J. (Novartis AG; Novartis Deutschland GmbH); Indolophenanthidines, their preparation and use. DE 3402392; EP 0155903; ES 8606339; JP 1985197687; US 4634708 . |
| 【2】 Prous, J.; Castaner, J.; CY-208-243. Drugs Fut 1990, 15, 4, 344. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10463 | Benzoyl chloride | 98-88-4 | C7H5ClO | 详情 | 详情 | |
| (I) | 11143 | 1-Benzoyl-1,2,2a,5-tetrahydrobenzo[cd]indol-4(3H)-one | C18H15NO2 | 详情 | 详情 | |
| (II) | 11144 | N-(1-Benzoyl-1,2,2a,3-tetrahydrobenzo[cd]indol-4-yl)-N-methylbenzamide | C26H22N2O2 | 详情 | 详情 | |
| (III) | 11145 | (5aR,6aR,12bS)-4-Benzoyl-7-methyl-4,5,5a,6a,7,12b-hexahydroindolo[4,3-ab]phenanthridin-8(6H)-one | C26H22N2O2 | 详情 | 详情 | |
| (IV) | 11146 | (5aR,6aR,12bR)-7-Methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine | C19H20N2 | 详情 | 详情 |