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【结 构 式】 
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【分子编号】48063 【品名】benzyl 4-aminocyclohexanecarboxylate 【CA登记号】 |
【 分 子 式 】C14H19NO2 【 分 子 量 】233.3104 【元素组成】C 72.07% H 8.21% N 6% O 13.72% |
合成路线1
该中间体在本合成路线中的序号：(VI)The known 2-(2-methoxyethoxymethyl)-3-[1-(phenacyloxycarbonyl)cyclopentyl]propanoic acid (I) was esterified with 5-indanol (II) by using EDC and HOBt to afford the indanyl ester (III). The phenacyl ester group was then reductively cleaved with Zn in HOAc to yield the racemic carboxylic acid (IV). Resolution of (IV) by means of (+)-pseudoephedrine provided the (S)-enantiomer (V). The chiral acid (V) was then coupled with benzyl cis-4-amino-1-cyclohexancarboxylate (VI) in the presence of EDC and HOBt to furnish amide (VII). The benzyl ester group of (VII) was finally cleaved by hydrogenolysis over Pd/C to give the title compound.
| 【1】 Williams, M.T.; Danilewicz, J.C. (Pfizer Inc.); Enantiomeric glutaramide diuretic agents. EP 0342850 . |
| 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) | 48058 | 3-(2-methoxyethoxy)-2-([1-[(2-oxo-2-phenylethoxy)carbonyl]cyclopentyl]methyl)propionic acid | C21H28O7 | 详情 | 详情 | |
| (II) | 48059 | 5-indanol | 1470-94-6 | C9H10O | 详情 | 详情 |
| (III) | 48060 | 2-oxo-2-phenylethyl 1-[3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentanecarboxylate | C30H36O7 | 详情 | 详情 | |
| (IV) | 48061 | 1-[3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentanecarboxylic acid | C22H30O6 | 详情 | 详情 | |
| (V) | 48062 | 1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentanecarboxylic acid | C22H30O6 | 详情 | 详情 | |
| (VI) | 48063 | benzyl 4-aminocyclohexanecarboxylate | C14H19NO2 | 详情 | 详情 | |
| (VII) | 48064 | benzyl 4-[[(1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl)carbonyl]amino]cyclohexanecarboxylate | C36H47NO7 | 详情 | 详情 |