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【结 构 式】 
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【分子编号】37783 【品名】1-[[(1R)-3-chloro-1-phenylpropyl]oxy]-2-methoxybenzene; (1R)-3-chloro-1-phenylpropyl 2-methoxyphenyl ether 【CA登记号】 |
【 分 子 式 】C16H17ClO2 【 分 子 量 】276.76248 【元素组成】C 69.44% H 6.19% Cl 12.81% O 11.56% |
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) that are separated by column chromatography. The condensation of alcohol (IV) with 2-methoxyphenol (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 |
|---|---|---|---|---|---|---|
| 11021 | Methanamine; Methylamine | 74-89-5 | CH5N | 详情 | 详情 | |
| (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) | 13182 | Guaiacol; 2-Methoxyphenol | 90-05-1 | C7H8O2 | 详情 | 详情 |
| (VI) | 37783 | 1-[[(1R)-3-chloro-1-phenylpropyl]oxy]-2-methoxybenzene; (1R)-3-chloro-1-phenylpropyl 2-methoxyphenyl ether | C16H17ClO2 | 详情 | 详情 |