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【结 构 式】 
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【分子编号】34897 【品名】3-oxo-3-phenylpropanenitrile 【CA登记号】614-16-4 |
【 分 子 式 】C9H7NO 【 分 子 量 】145.16072 【元素组成】C 74.47% H 4.86% N 9.65% O 11.02% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(I)The enantioselective reduction of 2-benzoylacetonitrile (I) with BH3/Me2S complex catalyzed by the chiral catalyst (II) in THF gives 3(S)-hydroxy-3-phenylpropylamine (III), which is protected with tert-butyl dicarbonate and NaOH to yield the carbamate (IV). The condensation of (IV) with 4-(trifluoromethyl)phenol (V) by means of triphenylphosphine and diethyl azodicarboxylate (DEAD) in THF affords N-[3(S)-phenyl-3-[4-(trifluoromethyl) phenoxy]propyl]carbamic acid tert-butyl ester (VI), which is finally reduced with LiAlH4 in refluxing THF to give the target (S)-Fluoxetine.
| 【1】 Jurgens, A.R.; Hilborn, J.W. (Sepracor Inc.); Fluoxetine process from benzoylacetonitrile. WO 0007976 . |
| 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) | 34897 | 3-oxo-3-phenylpropanenitrile | 614-16-4 | C9H7NO | 详情 | 详情 |
| (II) | 34898 | (3aR,8aS)-2-methyl-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d][1,3,2]oxazaborole | C10H12BNO | 详情 | 详情 | |
| (III) | 34899 | (1S)-3-amino-1-phenyl-1-propanol | C9H13NO | 详情 | 详情 | |
| (IV) | 34900 | tert-butyl (3S)-3-hydroxy-3-phenylpropylcarbamate | C14H21NO3 | 详情 | 详情 | |
| (V) | 33607 | 4-(trifluoromethyl)phenol | 402-45-9 | C7H5F3O | 详情 | 详情 |
| (VI) | 34901 | tert-butyl (3S)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylcarbamate | C21H24F3NO3 | 详情 | 详情 |
Extended Information