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【结 构 式】 
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【分子编号】40938 【品名】6-(1-pyrrolidinyl)-7,8-dihydro-2-naphthalenol 【CA登记号】 |
【 分 子 式 】C14H17NO 【 分 子 量 】215.29512 【元素组成】C 78.1% H 7.96% N 6.51% O 7.43% |
合成路线1
该中间体在本合成路线中的序号：(III)Enamine (III), prepared from beta-tetralone (I) by condensation with pyrrolidine (II) in refluxing benzene, was alkylated with bromoacetonitrile to provide, after hydrolytic treatment, keto nitrile (IV). Reductive amination of (IV) with ammonium acetate and NaBH3CN in MeOH furnished the benzo[e]indole tricyclic derivative (V), isolated as the hydrochloride salt. Coupling of (V) with trans-4-[(benzenesulfonamido) methyl]cyclohexanecarboxylic acid (VI) using O-benzotriazol-1-yl-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HBTU) gave amide (VII). This was finally reduced to the corresponding amine employing LiAlH4 in THF.
| 【1】 Wilson, S.J.; Dax, S.L.; Nepomuceno, D.H.; McNally, J.J.; Youngman, M.A.; Lovenverg, T.W.; N-(Sulfonamido)alkyl[tetrahydro-1H-benzo[e]indol-2-yl]amines: Potent antagonists of human neuropeptide Y Y5 receptor. Bioorg Med Chem Lett 2000, 10, 3, 213. |
| 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) | 40937 | 6-hydroxy-3,4-dihydro-2(1H)-naphthalenone | C10H10O2 | 详情 | 详情 | |
| (II) | 11376 | Pyrrolidine | 123-75-1 | C4H9N | 详情 | 详情 |
| (III) | 40938 | 6-(1-pyrrolidinyl)-7,8-dihydro-2-naphthalenol | C14H17NO | 详情 | 详情 | |
| (IV) | 40939 | 2-(6-hydroxy-2-oxo-1,2,3,4-tetrahydro-1-naphthalenyl)acetonitrile | C12H11NO2 | 详情 | 详情 | |
| (V) | 40940 | (3aS,9bR)-2-amino-3a,4,5,9b-tetrahydro-1H-benzo[e]indol-7-ol | C12H14N2O | 详情 | 详情 | |
| (VI) | 37020 | 4-[[(phenylsulfonyl)amino]methyl]cyclohexanecarboxylic acid | C14H19NO4S | 详情 | 详情 | |
| (VII) | 40941 | N-[(3aS,9bR)-7-hydroxy-3a,4,5,9b-tetrahydro-1H-benzo[e]indol-2-yl]-4-[[(phenylsulfonyl)amino]methyl]cyclohexanecarboxamide | C26H31N3O4S | 详情 | 详情 |