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【结 构 式】 
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【分子编号】59008 【品名】1-adamantylformamide 【CA登记号】 |
【 分 子 式 】C11H17NO 【 分 子 量 】179.26212 【元素组成】C 73.7% H 9.56% N 7.81% O 8.93% |
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：(V)Opening of the known lactone (I) with HBr in HOAc produces the racemic cis bromo-acid (II). Acid (II) is then converted to the corresponding methyl ester (III) by chlorination with SOCl2, followed by treatment with methanolic HCl. Acylation of 1-adamantanamine (IV) with ethyl formate yields the formamide (V), which is subsequently reduced to the N-methyl amine (VI) employing LiAlH4 in THF. Finally, alkylation of the secondary amine (VI) with bromo ester (III) in the presence of NaHCO3 in hot DMF gives rise to the title compound.
| 【1】 Ronsisvalle, G.; et al.; Substituted 1-phenyl-2-cyclopropylmethylamines with high affinity and selectively for sigma sites. Bioorg Med Chem 2000, 8, 6, 1503. |
| 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) | 28144 | 1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one | C11H10O2 | 详情 | 详情 | |
| (II) | 59006 | (1S,2R)-2-(bromomethyl)-1-phenylcyclopropanecarboxylic acid | C11H11BrO2 | 详情 | 详情 | |
| (III) | 59007 | methyl (1S,2R)-2-(bromomethyl)-1-phenylcyclopropanecarboxylate | C12H13BrO2 | 详情 | 详情 | |
| (IV) | 53978 | 1-Adamantanamine; 1-Adamantylamine; 1-Aminoadamantane | 768-94-5 | C10H17N | 详情 | 详情 |
| (V) | 59008 | 1-adamantylformamide | C11H17NO | 详情 | 详情 | |
| (VI) | 59009 | N-(1-adamantyl)-N-methylamine; N-methyl-1-adamantanamine | C11H19N | 详情 | 详情 |
Extended Information