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【结 构 式】 
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【分子编号】56311 【品名】tert-butyl 4-(phenylsulfonyl)-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C16H23NO4S 【 分 子 量 】325.42896 【元素组成】C 59.05% H 7.12% N 4.3% O 19.67% S 9.85% |
合成路线1
该中间体在本合成路线中的序号：(IV)The (phenylsulfanyl)piperidine (III) was obtained by condensation of N-Boc-4-piperidinol (I) with diphenyl disulfide (II) in the presence of tributylphosphine. Subsequent oxidation of sulfide (III) to the corresponding sulfone (IV) was achieved using oxone® on wet alumina. Deprotection of the N-Boc-piperidine (IV) with HCl afforded piperidine (V), which was finally alkylated with 2-bromo-4'-fluoroacetophenone (VI) to furnish the title N-phenacyl piperidine.
| 【1】 Blurton, P.; Burkamp, F.; Fletcher, S.R.; et al.; 4-(Phenylsulfonyl)piperidines: Novel, selective, and biovailable 5-HT2A receptor antagonists. J Med Chem 2002, 45, 2, 492. |
| 【2】 Macleod, A.M.; Blurton, P.; Fletcher, S.R.; Van Niel, M.B.; Burkamp, F.; Cheng, S.K.-F. (Merck Sharp & Dohme Ltd.); Phenylsulphonyl derivs. as 5-HT receptor ligands. EP 1147083; WO 0043362 . |
| 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) | 18625 | tert-butyl 4-hydroxy-1-piperidinecarboxylate | C10H19NO3 | 详情 | 详情 | |
| (II) | 17473 | diphenyl disulfide; 1-(phenyldisulfanyl)benzene; diphenyldisulfide | 882-33-7 | C12H10S2 | 详情 | 详情 |
| (III) | 32561 | tert-butyl 4-(phenylsulfanyl)-1-piperidinecarboxylate | C16H23NO2S | 详情 | 详情 | |
| (IV) | 56311 | tert-butyl 4-(phenylsulfonyl)-1-piperidinecarboxylate | C16H23NO4S | 详情 | 详情 | |
| (V) | 56312 | 4-(phenylsulfonyl)piperidine; phenyl 4-piperidinyl sulfone | C11H15NO2S | 详情 | 详情 | |
| (VI) | 27904 | 2-bromo-1-(4-fluorophenyl)-1-ethanone | 403-29-2 | C8H6BrFO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)Condensation of indolyl acetohydrazide (I) with carbon disulfide in the presence of KOH afforded the potassium dithiocarbazate (II), which was further cyclized to the target aminotriazole thione upon refluxing with aqueous hydrazine.
| 【1】 Andreadou, I.; et al.; Antioxidant activity of novel indole derivatives and protection of the myocardial damage in rabbits. Chem Pharm Bull 2002, 50, 2, 165. |