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【结 构 式】 
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【分子编号】26220 【品名】1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid 【CA登记号】67123-97-1 |
【 分 子 式 】C10H11NO2 【 分 子 量 】177.20288 【元素组成】C 67.78% H 6.26% N 7.9% O 18.06% |
合成路线1
该中间体在本合成路线中的序号：(II)Pictet-Spengler condensation of phenylalanine (I) with formaldehyde and HCl provided tetrahydroisoquinoline (II). Reduction of the carboxylic acid (II) to alcohol (III) was then performed in the presence of borane and BF3-Et2O. Subsequent protection of amino and hydroxyl groups of (III) with carbonyl diimidazole in boiling THF produced the cyclic carbamate (IV). After chlorosulfonation of (IV), the resulting sulfonyl chloride (V) was treated with ammonia in acetonitrile to furnish sulfonamide (VI). Finally, basic hydrolysis of the oxazolidinone (VI), followed by acid decarboxylation yielded the title compound.
| 【1】 Teoh, B.; Dahanukar, V.H.; Criscione, K.R.; Grunewald, G.L.; 3,7-Disubstituted-1,2,3,4-tetrahydroisoquinolines display remarkable potency and selectivity as inhibitors of phenylethanolamine N-methyltransferase versus the alpha2-Adrenoceptor1a. J Med Chem 1999, 42, 11, 1982. |
| 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) | 26219 | Phenylalanine | 150-30-1 | C9H11NO2 | 详情 | 详情 |
| (II) | 26220 | 1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid | 67123-97-1 | C10H11NO2 | 详情 | 详情 |
| (III) | 26221 | 1,2,3,4-tetrahydro-3-isoquinolinylmethanol | C10H13NO | 详情 | 详情 | |
| (IV) | 26222 | 1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one | C11H11NO2 | 详情 | 详情 | |
| (V) | 26223 | 3-oxo-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinoline-7-sulfonyl chloride | C11H10ClNO4S | 详情 | 详情 | |
| (VI) | 26224 | 3-oxo-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinoline-7-sulfonamide | C11H12N2O4S | 详情 | 详情 |