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【结 构 式】 
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【分子编号】33037 【品名】tert-butyl 4-[2-[7-cyano-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]cyclohexylcarbamate 【CA登记号】 |
【 分 子 式 】C23H33N3O2 【 分 子 量 】383.53404 【元素组成】C 72.03% H 8.67% N 10.96% O 8.34% |
合成路线1
该中间体在本合成路线中的序号：(XV)An alternative procedure started from trans-4-aminocyclohexylacetic acid hydrogen sulfate (XI), which was esterified with methanol and sulfuric acid to give aminoester (XII). Protection of the amino group of (XII) as the tert-butyl carbamate (XIII), followed by ester reduction with DIBAL gave rise to aldehyde (XIV). Reductive condensation of (XIV) with tetrahydroisoquinoline (IV) provided (XV). The Boc group of (XV) was then cleaved with trifluoroacetic acid to furnish the trans amine (XVI). This was finally converted to the target compound by coupling with indole-2-carboxylic acid (X) as above.
| 【1】 Stokker, G.E.; Preparation of 1,2,3,4-tetrahydroisoquinolines lacking electron donating groups - an intramolecular cyclization complementary to the Pictet-Spengler reaction. Tetrahedron Lett 1996, 37, 31, 5453. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 33026 | 1,2,3,4-tetrahydro-7-isoquinolinecarbonitrile | C10H10N2 | 详情 | 详情 | |
| (X) | 25226 | 1H-Indole-2-carboxylic acid; Indole-2-carboxylic acid | 1477-50-5 | C9H7NO2 | 详情 | 详情 |
| (XI) | 33033 | 2-(4-aminocyclohexyl)acetic acid | C8H15NO2 | 详情 | 详情 | |
| (XII) | 33034 | methyl 2-(4-aminocyclohexyl)acetate | C9H17NO2 | 详情 | 详情 | |
| (XIII) | 33035 | methyl 2-[4-[(tert-butoxycarbonyl)amino]cyclohexyl]acetate | C14H25NO4 | 详情 | 详情 | |
| (XIV) | 33036 | tert-butyl 4-(2-oxoethyl)cyclohexylcarbamate | C13H23NO3 | 详情 | 详情 | |
| (XV) | 33037 | tert-butyl 4-[2-[7-cyano-3,4-dihydro-2(1H)-isoquinolinyl]ethyl]cyclohexylcarbamate | C23H33N3O2 | 详情 | 详情 | |
| (XVI) | 33038 | 2-[2-(4-aminocyclohexyl)ethyl]-1,2,3,4-tetrahydro-7-isoquinolinecarbonitrile | C18H25N3 | 详情 | 详情 |