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【结 构 式】 
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【药物名称】 【化学名称】(1S,2R)-2-[1(S)-Aminopropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide 【CA登记号】 【 分 子 式 】C19H30N2O 【 分 子 量 】302.46375 |
【开发单位】Asahi Kasei (Originator) 【药理作用】Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, NMDA Antagonists |
合成路线1
The title compound is synthesized from the optically active lactone (I). Aluminum chloride-catalyzed aminolysis of (I) with dipropylamine affords the hydroxy amide (II). Subsequent Swern oxidation of the alcohol function of (II) leads to aldehyde (III). Addition of ethylmagnesium bromide to aldehyde (III) then stereoselectively provides the (S)-alcohol adduct (IV). Introduction of an azido group in (IV) by using a Mitsunobu-type reaction leads to configuration-retained azide (V). This is finally reduced to the desired amine by catalytic hydrogenation in the presence of Pd/C
| 【1】 Kazuta, Y.; et al.; Synthesis of (1S,2R)-1-phenyl-2-[(S)-1-aminopropyl]-N, N-diethylcyclopropanecarboxamide (PPDC) derivatives modified at the carbamoyl moiety as a new class of NMDA receptor antagonists. Bioorg. Med. Chem. 2002, 10, 6, 1777. |
| 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) | 61470 | (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one | 63106-93-4 | C11H10O2 | 详情 | 详情 |
| (II) | 61471 | (1S,2R)-2-(hydroxymethyl)-1-phenyl-N,N-dipropylcyclopropanecarboxamide | C17H25NO2 | 详情 | 详情 | |
| (III) | 61472 | (1S,2R)-2-formyl-1-phenyl-N,N-dipropylcyclopropanecarboxamide | C17H23NO2 | 详情 | 详情 | |
| (IV) | 61473 | (1S,2R)-2-[(1S)-1-hydroxypropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide | C19H29NO2 | 详情 | 详情 | |
| (V) | 61474 | (1S,2R)-2-[(1S)-1-azidopropyl]-1-phenyl-N,N-dipropylcyclopropanecarboxamide | C19H28N4O | 详情 | 详情 |