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【结 构 式】 
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【分子编号】58229 【品名】methyl 2-[4-(4-{4-[hydroxy(diphenyl)methyl]-1-piperidinyl}-4-oxobutanoyl)phenyl]-2-methylpropanoate 【CA登记号】 |
【 分 子 式 】C33H37NO5 【 分 子 量 】527.66052 【元素组成】C 75.12% H 7.07% N 2.65% O 15.16% |
合成路线1
该中间体在本合成路线中的序号：(V)The Friedel Craft's condensation of 2-methyl-2-phenylpropionic acid methyl ester (I) with succinic anhydride (II) by means of AlCl3 in CS2 or dichloromethane/nitrobenzene gives 2-[4-(hydroxysuccinyl)phenyl]-2-methylpropionic acid methyl ester (III) (purified through its phenethylamine salt), which is condensed with 4-(1-hydroxy-1,1-diphenylmethyl)piperidine (IV) by means of ethyl chloroformate and TEA in THF or with DCC and p-nitrophenol in ethyl acetate to yield the adduct (V). The reduction of the oxo groups of (V) by means of BH3/Me2S in THF affords the ester precursor (VI), which is finally hydrolyzed with NaOH in refluxing methanol to provide the target compound.
| 【1】 Schroeder, C.; Huddleston, R.; Charles, R. (Aventis Pharma Deutschland GmbH); Process for the production of the piperidine deriv. fexofenadine. WO 02102776 . |
| 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) | 58227 | methyl 2-methyl-2-phenylpropanoate; Methyl alpha,alpha-dimethylbenzeneacetate | C11H14O2 | 详情 | 详情 | |
| (II) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |
| (III) | 58228 | 4-[4-(2-methoxy-1,1-dimethyl-2-oxoethyl)phenyl]-4-oxobutanoic acid | C15H18O5 | 详情 | 详情 | |
| (IV) | 17178 | diphenyl(4-piperidinyl)methanol; alpha,alpha-Diphenyl-4-piperidinomethanol; Azacyclonol | 115-46-8 | C18H21NO | 详情 | 详情 |
| (V) | 58229 | methyl 2-[4-(4-{4-[hydroxy(diphenyl)methyl]-1-piperidinyl}-4-oxobutanoyl)phenyl]-2-methylpropanoate | C33H37NO5 | 详情 | 详情 | |
| (VI) | 58230 | methyl 2-[4-(1-hydroxy-4-{4-[hydroxy(diphenyl)methyl]-1-piperidinyl}butyl)phenyl]-2-methylpropanoate | C33H41NO4 | 详情 | 详情 |