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【结 构 式】 
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【分子编号】45030 【品名】5-nitro-1,3-benzodioxole 【CA登记号】 |
【 分 子 式 】C7H5NO4 【 分 子 量 】167.12104 【元素组成】C 50.31% H 3.02% N 8.38% O 38.29% |
合成路线1
该中间体在本合成路线中的序号：(III)A synthesis of [14C]-paroxetine labeled at the methylenedioxy group has been described: 4-Nitropyrocatechol (I) is cyclized with [14C]-CH2Br2 by means of cesium carbonate in DMSO, giving 3,4-(methylenedioxy)nitrobenzene (III). The reduction of (III) with H2 over Pd/C in ethanol yields the corresponding aniline (IV), which is treated with HNO2, copper nitrite and cuprous oxide to afford the corresponding phenol (V). The condensation of (V) with (3S,4R)-4-(4-fluorophenyl)-1-methyl-3-(phenylsulfonyloxymethyl)piperidine (VI) by means of sodium methoxide in methanol gives [14C]-labeled 1-methylparoxetine (VII), which is finally demethylated with vinyl chloroformate and potassium carbonate in dichloroethane.
| 【1】 Lawrie, K.W.M.; Rustidge, D.C.; The synthesis of [methylene-14C]paroxetine BRL 29060A. J Label Compd Radiopharm 1993, 33, 8, 777. |
| 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) | 10982 | 4-Nitrocatechol; 4-Nitro-1,2-benzenediol; 1,2-Dihydroxy-4-nitrobenzene | 3316-09-4 | C6H5NO4 | 详情 | 详情 |
| (III) | 10983 | 1,2-(Methylenedioxy)-4-nitrobenzene; 5-Nitro-1,3-benzodioxole | 2620-44-2 | C7H5NO4 | 详情 | 详情 |
| (III) | 45030 | 5-nitro-1,3-benzodioxole | C7H5NO4 | 详情 | 详情 | |
| (IV) | 10984 | 1,3-Benzodioxol-5-amine; 1,3-Benzodioxol-5-ylamine.; 3,4-(Methylenedioxy)aniline | 14268-66-7 | C7H7NO2 | 详情 | 详情 |
| (IV) | 45031 | 1,3-benzodioxol-5-amine; 1,3-benzodioxol-5-ylamine | C7H7NO2 | 详情 | 详情 | |
| (V) | 10985 | 1,3-Benzodioxol-5-ol; Sesamol | 533-31-3 | C7H6O3 | 详情 | 详情 |
| (V) | 45032 | 1,3-benzodioxol-5-ol | C7H6O3 | 详情 | 详情 | |
| (VI) | 10986 | [(3S,4R)-4-(4-fluorophenyl)-1-methylhexahydro-3-pyridinyl]methyl benzenesulfonate | C19H22FNO3S | 详情 | 详情 | |
| (VII) | 10987 | (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylhexahydropyridine; 1,3-Benzodioxol-5-yl [(3S,4R)-4-(4-fluorophenyl)-1-methylhexahydro-3-pyridinyl]methyl ether | C20H22FNO3 | 详情 | 详情 | |
| (VII) | 45033 | 1,3-benzodioxol-5-yl [(3S,4R)-4-(4-fluorophenyl)-1-methylpiperidinyl]methyl ether; (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-1-methylpiperidine | C20H22FNO3 | 详情 | 详情 | |
| (VIII) | 10988 | (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)hexahydropyridine; 1,3-Benzodioxol-5-yl [(3S,4R)-4-(4-fluorophenyl)hexahydro-3-pyridinyl]methyl ether | C19H20FNO3 | 详情 | 详情 | |
| (VIII) | 45039 | (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine; 1,3-benzodioxol-5-yl [(3S,4R)-4-(4-fluorophenyl)piperidinyl]methyl ether | C19H20FNO3 | 详情 | 详情 |