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【结 构 式】

【药物名称】Nisoxetine

【化学名称】(±)-3-(2-Methoxyphenoxy)-N-methyl-3-phenyl-1-propanamine

【CA登记号】53179-07-0

【 分 子 式 】C17H21NO2

【 分 子 量 】271.36242

【开发单位】Lilly (Originator)

【药理作用】Antidepressants, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS

合成路线1

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
Extended Information