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【结 构 式】 
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【分子编号】55294 【品名】4-[4-(dimethylamino)-1-hydroxy-1-(4-methylphenyl)butyl]-3-(hydroxymethyl)benzoic acid 【CA登记号】 |
【 分 子 式 】C21H27NO4 【 分 子 量 】357.44972 【元素组成】C 70.56% H 7.61% N 3.92% O 17.9% |
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)The reaction of 5-carboxyphthalide (I) with 4-fluorophenylmagnesium bromide (II) in THF gives the lactol (III), which is treated with 3-(dimethylamino)propylmagnesium chloride in the same solvent to yield the dihydroxylated intermediate (V). The cyclization of (V) by means of conc. HCl affords the isobenzofuran derivative (VI), which is finally treated with sulfamide and thionyl chloride in sulfolane at 130 C in order to convert the carboxy group of (VI) into the target 5-cyano group of citalopram.
| 【1】 Petersen, H.; Dancer, R.; Ahmadian, H. (H. Lundbeck A/S); Method for the preparation of citalopram. WO 0216341; WO 0216342 . |
| 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) | 37594 | 1-oxo-1,3-dihydro-2-benzofuran-5-carboxylic acid | C9H6O4 | 详情 | 详情 | |
| (II) | 13463 | o-Fluoronitrobenzene; 1-fluoro-2-nitrobenzene | 1493-27-2 | C6H4FNO2 | 详情 | 详情 |
| (III) | 55293 | 1-(4-fluorophenyl)-1-hydroxy-1,3-dihydro-2-benzofuran-5-carboxylic acid | C15H11FO4 | 详情 | 详情 | |
| (IV) | 12587 | Chloro[3-(dimethylamino)propyl]magnesium | C5H12ClMgN | 详情 | 详情 | |
| (V) | 55294 | 4-[4-(dimethylamino)-1-hydroxy-1-(4-methylphenyl)butyl]-3-(hydroxymethyl)benzoic acid | C21H27NO4 | 详情 | 详情 | |
| (VI) | 55295 | 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carboxylic acid | C20H22FNO3 | 详情 | 详情 |
Extended Information