methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Base Information

Chemical Name:methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate
CAS No.:186355-45-3
Molecular Formula:C₃₃H₃₃N₃O₉
Molecular Weight:615.64
Hs Code.:

methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Synonyms:methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

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Chemical Property of methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

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Technology Process of methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

There total 26 articles about methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

: 128781-07-7
5,6,7-trimethoxy-1H-indole-2-carboxylic acid

: 174956-24-2
methyl (2S,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

: 186355-45-3
methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: methyl (2S,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate; With hydrogenchloride; In methanol; at 0 ℃; for 1h;

5,6,7-trimethoxy-1H-indole-2-carboxylic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 4h;
DOI:10.1021/ja962431g

Reference yield:

: 128781-07-7
5,6,7-trimethoxy-1H-indole-2-carboxylic acid

: (2S,8S)-4-Benzyloxy-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylic acid methyl ester

: 186355-45-3
methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 4h; Yield given;
DOI:10.1021/ja953777e

Reference yield:

: 174956-23-1
methyl (2S,8S)-4-(benzyloxy)-8-[(tert-butyldimethylsilyl)oxy]-3,6-bis(tert-butyloxycarbonyl)-1-imino-2-methyl-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

: 186355-45-3
methyl (2S,8S)-4-(benzyloxy)-8-hydroxy-2-methyl-1-oxo-6-[(5,6,7-trimethoxyindol-2-yl)carbonyl]-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 85 percent / TsOH*H₂O; water / tetrahydrofuran / 2.5 h / 0 °C

2.1: HCl / methanol / 1 h / 0 °C

2.2: 68 percent / EDCI / dimethylformamide / 4 h / 25 °C

With hydrogenchloride; water; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1.1: Hydrolysis / 2.1: deprotection / 2.2: Acylation;
DOI:10.1021/ja962431g