【结 构 式】 |
【分子编号】26504 【品名】N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-phenyl-3-piperidinamine 【CA登记号】 |
【 分 子 式 】C23H30N2O 【 分 子 量 】350.50408 【元素组成】C 78.82% H 8.63% N 7.99% O 4.56% |
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:(VI)Reductive condensation of 3-amino-2-chloropyridine (I) with 5-isopropylbenzofuran-7-carbaldehyde (II) in the presence of sodium triacetoxyborohydride provided secondary amine (III). Displacement of the chlorine atom of (III) with phenylmagnesium bromide (IV) using NiCl2 produced phenylpyridine (V), which was hydrogenated with hydrogen over PtO2 in acetic acid to give racemic piperidine (VI). Resolution of (VI) with (R)-(-)-mandelic acid yielded the (2S,3S)-isomer, which was finally isolated as the dihydrochloride salt.
【1】 Tanaoue, Y.; Beppu, K.; Okayama, A.; Sakamoto, O. (Hisamitsu Pharmaceutical Co., Ltd.); Piperidine derivs.. EP 0826684; US 5886011; WO 9630367 . |
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) | 11160 | 2-Chloro-3-pyridinamine; 2-Chloro-3-pyridinylamine; 3-Amino-2-chloropyridine; 2-Chloro-3-aminopyridine | 6298-19-7 | C5H5ClN2 | 详情 | 详情 |
(II) | 26501 | 5-isopropyl-2,3-dihydro-1-benzofuran-7-carbaldehyde | C12H14O2 | 详情 | 详情 | |
(III) | 26502 | 2-chloro-N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3-pyridinamine | C17H19ClN2O | 详情 | 详情 | |
(IV) | 17616 | bromo(phenyl)magnesium; Phenyl Magnesium Bromide | 100-58-3 | C6H5BrMg | 详情 | 详情 |
(V) | 26503 | N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-phenyl-3-pyridinamine | C23H24N2O | 详情 | 详情 | |
(VI) | 26504 | N-[(5-isopropyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-2-phenyl-3-piperidinamine | C23H30N2O | 详情 | 详情 |
Extended Information