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【结 构 式】

【分子编号】57776

【品名】ethyl 1-phenyl-3-(1H-pyrrol-1-yl)-1H-indene-2-carboxylate

【CA登记号】

【 分 子 式 】C22H19NO2

【 分 子 量 】329.3984

【元素组成】C 80.22% H 5.81% N 4.25% O 9.71%

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:(VII)

3-Phenylindan-1-one (III) is prepared by either condensation between cinnamic acid (I) and benzene in the presence of AlCl3 or by Friedel-Crafts cyclization of 3,3-diphenylpropionic acid (II) in hot polyphosphoric acid. Claisen condensation of indanone (III) with diethyl carbonate affords keto ester (IV), which is further converted to enamino ester (V) upon treatment with ammonium acetate in boiling EtOH. Clauson-Kaas condensation of aminoindene (V) with 2,5-dimethoxytetrahydrofuran (VI) provides a mixture of isomeric pyrrolyl indenes (VII) and (VIII). Subsequent reduction of this mixture with NaBH4/NiCl2 affords the epimeric mixture of indanes (IX). Alkaline hydrolysis of esters (IX) proceeds with epimerization at C-2 to furnish the trans-trans acid (X). After activation of acid (X) as the corresponding mixed anhydride with ethyl chloroformate, coupling with pyrrolidine yields the target amide.

1 Rault, S.; Jarry, C.; Bovy, P.R.; Sopkova, J.; Dallemagne, P.; Guillon, J.; Leger, J.-M.; Synthesis of a novel class of non-peptide NK-2 receptor ligand, derived from 1-phenyl-3-pyrrol-1-ylidan-2-carboxamides. Bioorg Med Chem 2002, 10, 4, 1043.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IXa) 57778 ethyl (1S,2S,3S)-1-phenyl-3-(1H-pyrrol-1-yl)-2,3-dihydro-1H-indene-2-carboxylate C22H21NO2 详情 详情
(IXb) 57779 ethyl (1S,2R,3S)-1-phenyl-3-(1H-pyrrol-1-yl)-2,3-dihydro-1H-indene-2-carboxylate C22H21NO2 详情 详情
(I) 37680 (2E)-3-phenyl-2-propenoic acid; trans-Cinnamic acid; trans-3-Phenylacrylic acid 140-10-3 C9H8O2 详情 详情
(II) 57773 3-Phenyl-1-indanone 16618-72-7 C15H12O 详情 详情
(III) 36717 3,3-diphenylpropionic acid 606-83-7 C15H14O2 详情 详情
(IV) 57774 ethyl (2R,3S)-1-oxo-3-phenyl-2,3-dihydro-1H-indene-2-carboxylate C18H16O3 详情 详情
(V) 57775 ethyl (1S)-3-amino-1-phenyl-1H-indene-2-carboxylate C18H17NO2 详情 详情
(VI) 12312 (2S)-3-[1-(tert-Butoxycarbonyl)-1H-imidazol-5-yl]-2-[[(2R)-4-(4-morpholinyl)-2-(1-naphthylmethyl)-4-oxobutanoyl]amino]propionic acid C30H36N4O7 详情 详情
(VII) 57776 ethyl 1-phenyl-3-(1H-pyrrol-1-yl)-1H-indene-2-carboxylate C22H19NO2 详情 详情
(VIII) 57777 ethyl 3-phenyl-1-(1H-pyrrol-1-yl)-1H-indene-2-carboxylate C22H19NO2 详情 详情
(X) 57780 (1S,2R,3S)-1-phenyl-3-(1H-pyrrol-1-yl)-2,3-dihydro-1H-indene-2-carboxylic acid C20H17NO2 详情 详情
Extended Information