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【结 构 式】 
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【分子编号】61645 【品名】methyl (1R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C15H14Cl2O3 【 分 子 量 】313.17976 【元素组成】C 57.53% H 4.51% Cl 22.64% O 15.33% |
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：(IV)Treatment of methyl 3-hydroxy-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate (I) with N-phenyl trifluoromethanesulfonimide leads to the vinyl triflate (II). Suzuki coupling of triflate (II) with 3,4-dichlorophenylboronic acid (III) furnishes the oxabicyclooctene adduct (IV), which is further reduced to the oxabicyclooctane (V) with SmI2. Ester reduction in (V) with LiAlH4 provides alcohol (VI). This is finally esterified with 4-pentenoyl chloride (VII) to furnish the title compound.
| 【1】 Meltzer, P.C.; Liu, S.; Blanchette, H.; Blundell, P.; Madras, B.; Design and synthesis of an irreversible dopamine-sparing cocaine antagonist. Bioorg Med Chem 2002, 10, 11, 3583. |
| 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) | 61643 | methyl (1R,5S)-3-hydroxy-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate | C9H12O4 | 详情 | 详情 | |
| (II) | 61644 | methyl (1R,5S)-3-{[(trifluoromethyl)sulfonyl]oxy}-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate | C10H11F3O6S | 详情 | 详情 | |
| (III) | 34040 | 3,4-Dichlorophenylboronic acid | 151169-75-4 | C6H5BCl2O2 | 详情 | 详情 |
| (IV) | 61645 | methyl (1R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate | C15H14Cl2O3 | 详情 | 详情 | |
| (V) | 61646 | methyl (1R,2S,3R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]octane-2-carboxylate | C15H16Cl2O3 | 详情 | 详情 | |
| (VI) | 61647 | [(1R,2R,3R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]oct-2-yl]methanol | C14H16Cl2O2 | 详情 | 详情 | |
| (VII) | 61648 | 4-PENTENOYL CHLORIDE | C5H7ClO | 详情 | 详情 |
Extended Information