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【结 构 式】 
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【分子编号】56159 【品名】methyl 2-{[3-((2R)-2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}propyl)-1H-indol-7-yl]oxy}acetate 【CA登记号】 |
【 分 子 式 】C22H25ClN2O4 【 分 子 量 】416.90428 【元素组成】C 63.38% H 6.04% Cl 8.5% N 6.72% O 15.35% |
合成路线1
该中间体在本合成路线中的序号：(VIIIa)Alkylation of 7-hydroxyindole (I) with methyl chloroacetate (II) provided indolyl ether (III). Conjugate addition of 2-nitropropene (IV) to indole (III) in refluxing benzene, afforded the 3-(2-nitropropyl)indole (V), which was further reduced to the corresponding amine (VI) by catalytic hydrogenation over Raney nickel. Ring opening of the chiral epoxide (VII) with the racemic amine (VI) gave rise to a diastereomeric mixture of amino alcohols (VIII). After isolation of the desired (R,R)-isomer by column chromatography, basic hydrolysis of the methyl ester function yielded the title carboxylic acid.
| 【1】 Kato, S.; Harada, H.; Hirokawa, Y.; Yoshida, N.; Kawashima, H. (Dainippon Pharmaceutical Co., Ltd.); Indole derivs.. EP 0801059; JP 1996231504; US 5817689; WO 9616938 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIIa) | 56159 | methyl 2-{[3-((2R)-2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}propyl)-1H-indol-7-yl]oxy}acetate | C22H25ClN2O4 | 详情 | 详情 | |
| (VIIIb) | 56160 | methyl 2-{[3-((2S)-2-{[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino}propyl)-1H-indol-7-yl]oxy}acetate | C22H25ClN2O4 | 详情 | 详情 | |
| (I) | 56154 | 7-Hydroxyindole; 7-Indolol | 2380-84-9 | C8H7NO | 详情 | 详情 |
| (II) | 10257 | methyl 2-chloroacetate; methyl chloroacetate | 96-34-4 | C3H5ClO2 | 详情 | 详情 |
| (III) | 56155 | methyl 2-(1H-indol-7-yloxy)acetate | C11H11NO3 | 详情 | 详情 | |
| (IV) | 56156 | 2-nitro-1-propene | C3H5NO2 | 详情 | 详情 | |
| (V) | 56157 | methyl 2-{[3-(2-nitropropyl)-1H-indol-7-yl]oxy}acetate | C14H16N2O5 | 详情 | 详情 | |
| (VI) | 56158 | methyl 2-{[3-(2-aminopropyl)-1H-indol-7-yl]oxy}acetate | C14H18N2O3 | 详情 | 详情 | |
| (VII) | 15271 | (R)-(+)-3-Chlorostyrene oxide; (2R)-2-(3-Chlorophenyl)oxirane | 62600-71-9 | C8H7ClO | 详情 | 详情 |