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【结 构 式】

【分子编号】10080

【品名】(5-Oxo-2-pyrrolidinyl)methyl phenylmethanesulfonate

【CA登记号】

【 分 子 式 】C12H15NO4S

【 分 子 量 】269.32144

【元素组成】C 53.52% H 5.61% N 5.2% O 23.76% S 11.91%

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:(III)

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
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