methyl 2-{[3-(2-aminopropyl)-1H-indol-7-yl]oxy}acetate -Drug Synthesis Database

【结构式】

【分子编号】56158

【品名】methyl 2-{[3-(2-aminopropyl)-1H-indol-7-yl]oxy}acetate

【CA登记号】

【分子式】C₁₄H₁₈N₂O₃

【分子量】262.3086

【元素组成】C 64.11% H 6.92% N 10.68% O 18.3%

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：(VI)

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.

参考文献中间体

合成目标

【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

Extended Information