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【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%

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:(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
Extended Information