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【结 构 式】 
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【分子编号】52352 【品名】1-bromo-3,5-dimethyltricyclo[3.3.1.1~3,7~]decane 【CA登记号】 |
【 分 子 式 】C12H19Br 【 分 子 量 】243.18686 【元素组成】C 59.27% H 7.87% Br 32.86% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 1-bromo-3,5-dimethyladamantane (I) with Li in ethyl ether gives the corresponding lithium derivative, which is treated with NH2-Cl (II) to afford the target 1-aminoadamantane.
合成路线2
该中间体在本合成路线中的序号：(I)1-Bromo-3,5-dimethyladamantane (I) is subjected to Ritter reaction with acetonitrile in the presence of H2SO4 to produce acetamide (II). This is further hydrolyzed to the aminoadamantane (III) employing NaOH in refluxing diethyleneglycol. Condensation of amine (III) with maleic anhydride (IV) leads to the maleamic acid (V), which is finally cyclized to the target maleimide upon heating in acetic anhydride in the presence of NaOAc.
| 【1】 Wang, J.J.; Chern, Y.-T.; Liu, T.-Y.; Chi, C.-W.; In vitro and in vivo growth inhibition of cancer cells by adamantylmaleimide derivatives. Anti-Cancer Drug Des 1998, 13, 7, 779. |
| 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) | 52352 | 1-bromo-3,5-dimethyltricyclo[3.3.1.1~3,7~]decane | C12H19Br | 详情 | 详情 | |
| (II) | 63743 | N-(3,5-dimethyltricyclo[3.3.1.1~3,7~]dec-1-yl)acetamide | C14H23NO | 详情 | 详情 | |
| (III) | 63744 | 3,5-dimethyltricyclo[3.3.1.1~3,7~]dec-1-ylamine; 3,5-dimethyltricyclo[3.3.1.1~3,7~]decan-1-amine | C12H21N | 详情 | 详情 | |
| (IV) | 11182 | 2,5-Furandione; Maleic anhydride | 108-31-6 | C4H2O3 | 详情 | 详情 |
| (V) | 63745 | 4-[(3,5-dimethyltricyclo[3.3.1.1~3,7~]dec-1-yl)amino]-4-oxo-2-butenoic acid | C16H23NO3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)
| 【1】 Merli v. 2006. Process for the preparation of l-amino-3, 5-dimethyladamantane hydrochloride. W02006076562[本专利为Teva Pharmaceutical USA Inc.(US)所有] |
| 【2】 Zou Y, Xiong XY, Mei QB. 2003. Synthesis of memantine hydrochloride. 中国医药工业杂志．34 (5)：213～214 |
合成路线4
该中间体在本合成路线中的序号：(II)
| 【1】 Shukla S.2006．Process for preparing memantine. W0 2006122238（本专利为Dr. Reddy's laboratories Ltd所有） |