|
【结 构 式】 
|
【分子编号】43893 【品名】2-[2-(hydroxymethyl)phenyl]acetonitrile 【CA登记号】 |
【 分 子 式 】C9H9NO 【 分 子 量 】147.1766 【元素组成】C 73.45% H 6.16% N 9.52% O 10.87% |
合成路线1
该中间体在本合成路线中的序号：(VII)Synthesis of intermediate 5-[2-(bromomethyl)benzyl]-2-(triphenylmethyl)-2H-tetrazole (X): The reduction of 2-(cyanomethyl)benzoic acid (VI) with I2 and NaBH4 in THF gives 2-(cyanomethyl)benzyl alcohol (VII), which is cyclized with NaN3 and TEA in hot N-methylpyrrolidinone to yield 2-(1H-tetrazol-5-ylmethyl)benzyl alcohol (VIII). The reaction of (VIII) with trityl chloride and pyridine in dichloromethane affords the trityl protected compound (IX), which is finally brominated to the target intermediate (X) with NBS and Me2S in dichloromethane. Synthesis of intermediate 5-[2-(bromomethyl)benzyl]-2-(tetrahydropyran-2-yl)-2H-tetrazole (XII): The reaction of 2-(1H-tetrazol-5-ylmethyl)benzyl alcohol (VIII) with NBS and PPh3 in THF gives the 2-(1H-tetrazol-5-ylmethyl)benzyl bromide (XI), which is finally treated with dihydropyran (DHP) and pyridinium p-toluenesulfonate (PPTS) to yield the tetrahydropyranyl protected target intermediate (XII).
| 【1】 Sledeski, A.W.; et al.; A convergent synthesis of an LTD4 antagonist, RG12525. Tetrahedron Lett 1997, 38, 7, 1129. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 43892 | 2-(cyanomethyl)benzoic acid | C9H7NO2 | 详情 | 详情 | |
| (VII) | 43893 | 2-[2-(hydroxymethyl)phenyl]acetonitrile | C9H9NO | 详情 | 详情 | |
| (VIII) | 43894 | [2-(1H-1,2,3,4-tetraazol-5-ylmethyl)phenyl]methanol | C9H10N4O | 详情 | 详情 | |
| (IX) | 43895 | [2-[(2-trityl-2H-1,2,3,4-tetraazol-5-yl)methyl]phenyl]methanol | C28H24N4O | 详情 | 详情 | |
| (X) | 43896 | 5-[2-(bromomethyl)benzyl]-2-trityl-2H-1,2,3,4-tetraazole | C28H23BrN4 | 详情 | 详情 | |
| (XI) | 43897 | 5-[2-(bromomethyl)benzyl]-1H-1,2,3,4-tetraazole | C9H9BrN4 | 详情 | 详情 | |
| (XII) | 43898 | 5-[2-(bromomethyl)benzyl]-2-tetrahydro-2H-pyran-2-yl-2H-1,2,3,4-tetraazole | C14H17BrN4O | 详情 | 详情 |