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【结 构 式】 
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【分子编号】10006 【品名】Ethyl (3S)-3-hydroxy-3-phenylpropanoate; (-)-Ethyl (S)-3-hydroxy-3-phenylpropionate 【CA登记号】33401-74-0 |
【 分 子 式 】C11H14O3 【 分 子 量 】194.23036 【元素组成】C 68.02% H 7.27% O 24.71% |
合成路线1
该中间体在本合成路线中的序号：(III)A new synthesis for tomoxetine hydrochloride has been reported: The reduction of benzoylacetic acid ethyl ester (I) with Baker's yeast and glucose in water, or the enzymatic hydrolysis of 3-acetoxy-3-phenylpropionic acid ethyl ester (II), gives (-)-3-hydroxy-3-phenylpropionic acid ethyl ester (III), which by reaction with methylamine yields the corresponding amide (IV). The reduction of (IV) with LiAlH4 in ether affords (-)-3-hydroxy-N-methyl-3-phenylpropylamine (V), which is protected with di-tert-butyldicarbonate to the amide (VI). The condensation of (VI) with o-cresol (VII) by means of triphenylphosphine and diethylazodicarboxylate (DEAD) in ether yields the protected final product (VIII), which is finally deprotected with dry HCl in methanol.
| 【1】 Dike, S.Y.; Kumar, A.; Ner, D.H.; A new chemoenzymatic enantioselective synthesis of R-(-)-tomoxetine, (R)-fluoxetine and (S)-fluoxetine. Tetrahedron Lett 1991, 32, 16, 1901. |
| 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) | 10004 | Ethyl 3-oxo-3-phenylpropanoate; Benzoylacetic acid, ethyl ester | 94-02-0 | C11H12O3 | 详情 | 详情 |
| (II) | 10005 | Ethyl 3-(acetoxy)-3-phenylpropanoate | C13H16O4 | 详情 | 详情 | |
| (III) | 10006 | Ethyl (3S)-3-hydroxy-3-phenylpropanoate; (-)-Ethyl (S)-3-hydroxy-3-phenylpropionate | 33401-74-0 | C11H14O3 | 详情 | 详情 |
| (IV) | 10007 | (3S)-3-Hydroxy-N-methyl-3-phenylpropanamide | C10H13NO2 | 详情 | 详情 | |
| (V) | 10008 | (1S)-3-(Methylamino)-1-phenyl-1-propanol | 114133-37-8 | C10H15NO | 详情 | 详情 |
| (VI) | 10009 | tert-Butyl N-[(3S)-3-hydroxy-3-phenylpropyl]-N-methylcarbamate | C15H23NO3 | 详情 | 详情 | |
| (VII) | 10010 | o-Cresol | 95-48-7 | C7H8O | 详情 | 详情 |
| (VIII) | 10011 | tert-Butyl N-methyl-N-[(3R,4E,6Z)-3-(2-methylphenoxy)-4-vinyl-4,6-octadienyl]carbamate | C22H29NO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)
| 【1】 Kumar A, Ner DH, Dike SY. 1991.A new chemoenzjrnutic enantioselective synthesis of R-(?)-tomoxe-One, (R)- and (S)-fluoxetine. Tetnhedron Lett, 32r 1901~1904 |
| 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) | 10006 | Ethyl (3S)-3-hydroxy-3-phenylpropanoate; (-)-Ethyl (S)-3-hydroxy-3-phenylpropionate | 33401-74-0 | C11H14O3 | 详情 | 详情 |
| (II) | 10007 | (3S)-3-Hydroxy-N-methyl-3-phenylpropanamide | C10H13NO2 | 详情 | 详情 | |
| (III) | 10008 | (1S)-3-(Methylamino)-1-phenyl-1-propanol | 114133-37-8 | C10H15NO | 详情 | 详情 |
| (IV) | 10009 | tert-Butyl N-[(3S)-3-hydroxy-3-phenylpropyl]-N-methylcarbamate | C15H23NO3 | 详情 | 详情 | |
| (V) | 10011 | tert-Butyl N-methyl-N-[(3R,4E,6Z)-3-(2-methylphenoxy)-4-vinyl-4,6-octadienyl]carbamate | C22H29NO3 | 详情 | 详情 |