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【结 构 式】 
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【分子编号】34357 【品名】ethyl 3-[4-(benzyloxy)-1H-indol-3-yl]-4-methoxy-2-nitrobutanoate 【CA登记号】 |
【 分 子 式 】C22H24N2O6 【 分 子 量 】412.44244 【元素组成】C 64.07% H 5.87% N 6.79% O 23.28% |
合成路线1
该中间体在本合成路线中的序号：(VII)This compound can be prepared by two related ways: 1) The condensation of methoxyacetaldehyde (I) with isopropylamine (II) gives methoxyacetaldehyde isopropylimine (III), which is treated with 4-benzyloxyindole (IV) in acetic acid yielding 4-benzyloxy-3-(1-isopropylamino-2-ethoxyethyl)indole (V). The reaction of (V) with ethyl nitroacetate (VI) in hot toluene affords ethyl 3-(4-benzyloxyindol-3-yl)-2-nitro-5-oxahexanoate (VII), which is reduced with H2 over Raney-Ni in ethanol giving ethyl 3-(4-benzyloxyindol-3-yl)-2-amino-5-oxahexanoate (VIII). Finally, this compound is cyclized with paraformaldehyde (IX) in refluxing benzene. 2) Compound (VIII) can also be cyclized with glyoxylic acid (X) yielding a mixture of the tetrahydrocarboline (XI) and the dihydrocarboline (XII), which, without separation, are decarboxylated and dehydrogenated with sulfur at 140 C.
| 【1】 Neef, G.; Schmiechen, R.; Huth, A.; Eder, U.; Rathz, D.; Seidelmann, D.; Synthesis of 4-sibstituted beta-carbolines. Heterocycles 1983, 20, 7, 1295-1313. |
| 【2】 Neef, G.; Eder, U.; Schmiechen, R.; Huth, A.; Rathz, D.; Seidelmonn, D.; Kehr, W.; Palenschat, D.; Braestrup, C.T.; et al. (Schering AG); Pharmacologically active 3-substituted beta-carbolines. DD 161210; EP 0054507; ES 8301984; US 4435403; US 4596808 . |
| 【3】 Castaner, J.; Serradell, M.N.; ZK-91296. Drugs Fut 1984, 9, 10, 761. |
| 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) | 34354 | 2-methoxyacetaldehyde | 10312-83-1 | C3H6O2 | 详情 | 详情 |
| (II) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
| (III) | 34355 | N-[(E)-2-methoxyethylidene]-2-propanamine; N-isopropyl-N-[(E)-2-methoxyethylidene]amine | C6H13NO | 详情 | 详情 | |
| (IV) | 31535 | 4-Benzyloxyindole; 4-(benzyloxy)-1H-indole; benzyl 1H-indol-4-yl ether | 20289-26-3 | C15H13NO | 详情 | 详情 |
| (V) | 34356 | N-[1-[4-(benzyloxy)-1H-indol-3-yl]-2-methoxyethyl]-2-propanamine; N-[1-[4-(benzyloxy)-1H-indol-3-yl]-2-methoxyethyl]-N-isopropylamine | C21H26N2O2 | 详情 | 详情 | |
| (VI) | 15050 | ethyl 2-nitroacetate; Acetic acid, nitro-, ethyl ester | 626-35-7 | C4H7NO4 | 详情 | 详情 |
| (VII) | 34357 | ethyl 3-[4-(benzyloxy)-1H-indol-3-yl]-4-methoxy-2-nitrobutanoate | C22H24N2O6 | 详情 | 详情 | |
| (VIII) | 34358 | ethyl 2-amino-3-[4-(benzyloxy)-1H-indol-3-yl]-4-methoxybutanoate | C22H26N2O4 | 详情 | 详情 | |
| (X) | 15618 | 2-Oxoacetic acid; Glyoxylic Acid | 298-12-4 | C2H2O3 | 详情 | 详情 |
| (XI) | 34359 | 5-(benzyloxy)-3-(ethoxycarbonyl)-4-(methoxymethyl)-2,3,4,9-tetrahydro-1H-beta-carboline-1-carboxylic acid | C24H26N2O6 | 详情 | 详情 | |
| (XII) | 34360 | 5-(benzyloxy)-3-(ethoxycarbonyl)-4-(methoxymethyl)-2,4a,9,9a-tetrahydro-1H-beta-carboline-1-carboxylic acid | C24H26N2O6 | 详情 | 详情 |