【结 构 式】 |
【分子编号】10081 【品名】2-(5-Oxo-2-pyrrolidinyl)acetonitrile 【CA登记号】 |
【 分 子 式 】C6H8N2O 【 分 子 量 】124.1424 【元素组成】C 58.05% H 6.5% N 22.57% O 12.89% |
合成路线1
该中间体在本合成路线中的序号:(IV)The synthesis of [14C]-labeled vigabatrin has been described: The reduction by known methods of pyroglutamic acid (I) to the alcohol (II) and its acylation with p-toluenesulfonyl chloride gives 5-(tosyloxymethyl)pyrrolidin-2-one (III), which by reaction with [14C]-labeled sodium cyanide in hot DMF yields 5-([14C]-cyanomethyl)pyrrolidin-2-one (IV). The reduction of (VI) with H2 over Pd/Al2O3 and treatment with dimethylamine affords 5-[2-(dimethylamino)ethyl]pyrrolidin-2-one (VI), which is oxidized with H2O2 in water to the N-oxide (VI). The treatment of (VI) with K2CO3 in refluxing xylene affords 5-([14C]-vinyl)pyrrolidin-2-one (VII), which is finally submitted to ring opening with hot 5 M aqueous HCl, followed by neutralization with triethylamine.
【1】 Wagner, E.R.; Schuster, A.J.; Synthesis of carbon-14 labeled vigabatrin. J Label Compd Radiopharm 1993, 33, 3, 213. |
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) | 10078 | Pyrrolidonecarboxylic acid; 5-Oxo-proline; 5-Oxo-2-pyrrolidinecarboxylic acid | 149-87-1 | C5H7NO3 | 详情 | 详情 |
(II) | 10079 | 5-(Hydroxymethyl)-2-pyrrolidinone | 62400-75-3 | C5H9NO2 | 详情 | 详情 |
(III) | 10080 | (5-Oxo-2-pyrrolidinyl)methyl phenylmethanesulfonate | C12H15NO4S | 详情 | 详情 | |
(IV) | 10081 | 2-(5-Oxo-2-pyrrolidinyl)acetonitrile | C6H8N2O | 详情 | 详情 | |
(IV) | 44576 | 2-(5-oxo-2-pyrrolidinyl)acetonitrile | C6H8N2O | 详情 | 详情 | |
(V) | 10082 | 5-[2-(Dimethylamino)ethyl]-2-pyrrolidinone | C8H16N2O | 详情 | 详情 | |
(V) | 44577 | 5-[2-(dimethylamino)ethyl]-2-pyrrolidinone | C8H16N2O | 详情 | 详情 | |
(VI) | 10083 | dimethyl[2-(5-oxo-2-pyrrolidinyl)ethyl]ammoniumolate | C8H16N2O2 | 详情 | 详情 | |
(VI) | 44578 | dimethyl[2-(5-oxo-2-pyrrolidinyl)ethyl]ammoniumolate | C8H16N2O2 | 详情 | 详情 | |
(VII) | 10084 | 5-Vinyl-2-pyrrolidinol | C6H11NO | 详情 | 详情 | |
(VII) | 44579 | 5-vinyl-2-pyrrolidinol | C6H11NO | 详情 | 详情 |