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【结 构 式】

【分子编号】34356

【品名】N-[1-[4-(benzyloxy)-1H-indol-3-yl]-2-methoxyethyl]-2-propanamine; N-[1-[4-(benzyloxy)-1H-indol-3-yl]-2-methoxyethyl]-N-isopropylamine

【CA登记号】

【 分 子 式 】C21H26N2O2

【 分 子 量 】338.44972

【元素组成】C 74.53% H 7.74% N 8.28% O 9.45%

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:(V)

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
Extended Information