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【结 构 式】 
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【药物名称】LB-50016 【化学名称】2-[4-(3-Phenylpyrrolidin-1-yl)butyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide 【CA登记号】228579-02-0 【 分 子 式 】C21H24N2O3S 【 分 子 量 】384.50103 |
【开发单位】LG Chem (Originator) 【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, 5-HT1A Receptor Agonists |
合成路线1
The sulfonylation of 1-benzylpyrrolidin-3-ol by means of mesyl or tosyl chlorides gives the corresponding sulfonates (II) or (III), which are condensed with the diphenyl cuprate lithium (IV) yielding 1-benzyl-3-phenylpyrrolidine (V). The debenzylation of (V) with ammonium formate over Pd/C in methanol affords 3-phenylpyrrolidine (VI), which is finally condensed with 2-(4-bromobutyl)-1,2-benzoisothiazol-3-one S,S-dioxide (VII) by means of triethylamine in acetonitrile.
| 【1】 Lee, C.-H.; Ahn, K.H.; Lee, S.J.; Park, T.K.; Hong, C.Y.; N-Substituted-3-arylpyrrolidines: Potent and selective ligands at serotonin 1A receptor. Bioorg Med Chem Lett 1999, 9, 10, 1379. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 13975 | p-Toluenesulfonyl chloride;p-tosyl chloride;Toluene-4-sulfonyl chloride;4-Toluene sulfochloride;tosyl chloride; 4-Methylbenzenesulfonyl chloride | 98-59-9 | C7H7ClO2S | 详情 | 详情 | |
| (I) | 22746 | 1-benzyl-3-pyrrolidinol | C11H15NO | 详情 | 详情 | |
| (II) | 30988 | 1-benzyl-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]pyrrolidine | C14H21NOS | 详情 | 详情 | |
| (III) | 30989 | 1-benzyl-3-pyrrolidinyl 4-methylbenzenesulfonate | C18H21NO3S | 详情 | 详情 | |
| (V) | 30990 | 1-benzyl-3-phenylpyrrolidine | C17H19N | 详情 | 详情 | |
| (VI) | 30991 | 3-phenylpyrrolidine | C10H13N | 详情 | 详情 | |
| (VII) | 17043 | 2-(4-bromobutyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione | C11H12BrNO3S | 详情 | 详情 |