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【结 构 式】

【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%

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:(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
Extended Information