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【结 构 式】

【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%

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:(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
Extended Information