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【结 构 式】 
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【分子编号】16801 【品名】(1S)-1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)piperidino]-1-ethanol 【CA登记号】 |
【 分 子 式 】C20H23ClFNO 【 分 子 量 】347.8598632 【元素组成】C 69.06% H 6.66% Cl 10.19% F 5.46% N 4.03% O 4.6% |
合成路线1
该中间体在本合成路线中的序号：(S)-isomer2) The (R)- and (S)-enantiomers eliprodil are obtained as follows: The asymmetric dihydroxylation of 4-chlorostyrene (IV) by the Sharpless asymmetric dihydroxylation (AD) procedure (J Org Chem 1992, 57: 2768) methods alpha and beta (AD-alpha and AD-beta) gives both the (S)- and (R)-enantiomers of 1-(4-chlorophenyl)ethane-1,2-diol (Valpha) and (Vbeta), respectively. These compounds, by treatment first with methanesulfonyl chloride and then with K2CO3, yield the corresponding epoxides (VIalpha) and (VIbeta), respectively. Finally, both compounds are condensed with 4-(4-fluorobenzyl)piperidine (II) in refluxing isopropanol.
| 【1】 Di Fabio, R.; Thomas, R.J.; Pietra, C.; Ziviani, L.; The asymmetric synthesis of both enantiomers of eliprodil. Bioorg Med Chem Lett 1995, 5, 6, 551. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (Va) | 16797 | (1S)-1-(4-chlorophenyl)-1,2-ethanediol | C8H9ClO2 | 详情 | 详情 | |
| (Vb) | 16798 | (1R)-1-(4-chlorophenyl)-1,2-ethanediol | C8H9ClO2 | 详情 | 详情 | |
| (VIa) | 16799 | (2S)-2-(4-chlorophenyl)oxirane | C8H7ClO | 详情 | 详情 | |
| (VIb) | 16800 | (2R)-2-(4-chlorophenyl)oxirane | C8H7ClO | 详情 | 详情 | |
| (S)-isomer | 16801 | (1S)-1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)piperidino]-1-ethanol | C20H23ClFNO | 详情 | 详情 | |
| (R)-isomer | 16802 | (1R)-1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)piperidino]-1-ethanol | C20H23ClFNO | 详情 | 详情 | |
| (II) | 16794 | 4-(4-fluorobenzyl)piperidine | 92822-02-1 | C12H16FN | 详情 | 详情 |
| (IV) | 16796 | p-chlorostyrene; 1-chloro-4-vinylbenzene | 1073-67-2 | C8H7Cl | 详情 | 详情 |