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【结 构 式】 
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【分子编号】51408 【品名】3-ethyl 5-methyl 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate 【CA登记号】 |
【 分 子 式 】C18H20ClNO4 【 分 子 量 】349.81384 【元素组成】C 61.8% H 5.76% Cl 10.13% N 4% O 18.29% |
合成路线1
该中间体在本合成路线中的序号：(V)The cyclization of 2-butynoic acid methyl ester (I) with 2-(2-chlorobenzylidene)-3-oxobutyric acid ethyl ester (II) and benzylamine (III) in refluxing toluene gives the N-benzylated dihydropyridine (IV), which is debenzylated by reduction with formic acid over Pd/C in refluxing methanol to yield the dihydropyridine (V). The bromination of (V) with C5H5NH+ HBr3- in dichloromethane affords the bromomethyl compound (VI), which is condensed with 2-azidoethanol (VII) by means of NaH in ethyl ether to provide the 2-azidoethoxymethyl compound (VIII). Finally, the azido group of (VIII) is reduced with Zn and HCl in methanol to furnish the desired 2-aminoethoxymethyl compound.
| 【1】 Kim, S.-C.; et al.; Synthesis of amlodipine using aza Diels-Alder reaction. Bull Korean Chem Soc 2002, 23, 1, 143. |
| 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) | 51405 | 2-Butynoic acid methyl ester; Methyl 2-butynoate; Tetrolic acid methyl ester; Methyl tetrolate | 23326-27-4 | C5H6O2 | 详情 | 详情 |
| (II) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (III) | 51406 | ethyl (Z)-2-acetyl-3-(2-chlorophenyl)-2-propenoate | C13H13ClO3 | 详情 | 详情 | |
| (IV) | 51407 | 3-methyl 5-propyl 1-benzyl-4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate | C26H28ClNO4 | 详情 | 详情 | |
| (V) | 51408 | 3-ethyl 5-methyl 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate | C18H20ClNO4 | 详情 | 详情 | |
| (VI) | 51409 | 3-ethyl 5-methyl 2-(bromomethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylate | C18H19BrClNO4 | 详情 | 详情 | |
| (VII) | 24111 | 2-azido-1-ethanol | C2H5N3O | 详情 | 详情 | |
| (VIII) | 51410 | 5-methyl 3-propyl 2-[(2-azidoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydro-3,5-pyridinedicarboxylate | C21H25ClN4O5 | 详情 | 详情 |