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【结 构 式】 
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【分子编号】43106 【品名】1-[[(1R)-3-chloro-1-phenylpropyl]oxy]-4-(trifluoromethyl)benzene; (1R)-3-chloro-1-phenylpropyl 4-(trifluoromethyl)phenyl ether 【CA登记号】 |
【 分 子 式 】C16H14ClF3O 【 分 子 量 】314.7344696 【元素组成】C 61.06% H 4.48% Cl 11.26% F 18.11% O 5.08% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reduction of omega-chloropropiophenone (I) with NaBH4 in ethanol gives 3-chloro-1-phenyl-1-propanol (II), which is treated with butyric anhydride and pyridine in dichloromethane, yielding the corresponding racemic ester (III). The optical resolution of (III) with immobilized lipase B from Candida antarctica (CALB) affords a mixture of unreacted (S)-ester and (R)-alcohol (IV), which are separated by column chromatography. The condensation of alcohol (IV) with 4-(trifluoromethyl)phenol (V) by means of PPh3 and diethyl azodicarboxylate (DEAD) in THF gives the corresponding ether (VI), which is finally treated with methylamine in refluxing ethanol.
| 【1】 Anthonsen, T.; Ho, B.H.; Liu, H.L.; Chemoenzymatic synthesis of the non-tricyclic antidepressants fluoxetine, tomoxetine and nisoxetine. J Chem Soc - Perkins Trans I 2000, 11, 11, 1767. |
| 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) | 28073 | 3-chloro-1-phenyl-1-propanone | 936-59-4 | C9H9ClO | 详情 | 详情 |
| (II) | 28074 | 3-chloro-1-phenyl-1-propanol | C9H11ClO | 详情 | 详情 | |
| (III) | 37781 | 3-chloro-1-phenylpropyl butyrate | C13H17ClO2 | 详情 | 详情 | |
| (IV) | 37782 | (1R)-3-chloro-1-phenyl-1-propanol | C9H11ClO | 详情 | 详情 | |
| (V) | 33607 | 4-(trifluoromethyl)phenol | 402-45-9 | C7H5F3O | 详情 | 详情 |
| (VI) | 43106 | 1-[[(1R)-3-chloro-1-phenylpropyl]oxy]-4-(trifluoromethyl)benzene; (1R)-3-chloro-1-phenylpropyl 4-(trifluoromethyl)phenyl ether | C16H14ClF3O | 详情 | 详情 |