【结 构 式】 |
【分子编号】50723 【品名】(2R)-2-ethyl-2,3-dihydro-1-benzofuran-2-carbonitrile 【CA登记号】 |
【 分 子 式 】C11H11NO 【 分 子 量 】173.21448 【元素组成】C 76.28% H 6.4% N 8.09% O 9.24% |
合成路线1
该中间体在本合成路线中的序号:(VI)Alternatively, the title compound was prepared by an asymmetric synthesis: The known racemic 2-ethyl-2,3-dihydro-2-benzofurancarboxylic acid (II) was resolved by means of (S)-(+)-2-phenylglycinol to furnish the desired (+)-enantiomer (III). After esterification of (III) using MeOH in the presence of SOCl2, the resultant methyl ester (IV) was treated with ammonium hydroxide, yielding amide (V). Subsequent dehydration of amide (V) with P2O5 in refluxing toluene gave nitrile (VI). Treatment of (VI) with EtOH in the presence of a catalytic amount of NaOMe produced an intermediate imidate, which was subsequently treated with ethylenediamine and HCl to generate the title imidazoline.
【1】 Imbert, T.; Mayer, P. (Pierre Fabre Medicament); Method for preparing an optically pure benzofuran carboxylic acid and use thereof for preparing efaroxan. FR 2733983; US 5880296; WO 9635682 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(II) | 36673 | 2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid | C11H12O3 | 详情 | 详情 | |
(III) | 50720 | (2R)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid | C11H12O3 | 详情 | 详情 | |
(IV) | 50721 | methyl (2R)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylate | C12H14O3 | 详情 | 详情 | |
(V) | 50722 | (2R)-2-ethyl-2,3-dihydro-1-benzofuran-2-carboxamide | C11H13NO2 | 详情 | 详情 | |
(VI) | 50723 | (2R)-2-ethyl-2,3-dihydro-1-benzofuran-2-carbonitrile | C11H11NO | 详情 | 详情 |