methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Base Information

Chemical Name:methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate
CAS No.:186355-58-8
Molecular Formula:C₂₆H₃₀N₂O₇
Molecular Weight:482.533
Hs Code.:

Synonyms:methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

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

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

There total 9 articles about methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-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: 57.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 174873-34-8
methyl (2R,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

: 186355-58-8
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: methyl (2R,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;

di-tert-butyl dicarbonate; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/ja962431g

Reference yield:

: 174873-30-4
(3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[(tert-butyloxycarbonyl)amino]-5-cyano-1,2,3,4-tetrahydroquinoline

: 186355-58-8
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / NaH / dimethylformamide / 1 h / 0 °C

2.1: 12 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

3.1: 82 percent / LiOCH₃; CH₃OH / tetrahydrofuran / 1 h / 0 °C

4.1: 83 percent / TsOH*H₂O; water / tetrahydrofuran / 2 h / 0 °C

5.1: HCl / methanol / 1 h / 0 °C

5.2: 57 percent / tetrahydrofuran / 2 h / Heating

With hydrogenchloride; methanol; lithium methanolate; water; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Dieckmann condensation / 3.1: methanolysis / 4.1: Hydrolysis / 5.1: deprotection / 5.2: alkoxycarbonylation;
DOI:10.1021/ja962431g

Reference yield:

: (3S)-7-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]-1-(tert-butyloxycarbonyl)-6-[N-(tert-butyloxycarbonyl)-N-[1-[[(4S)-2-oxo-4-isopropyloxazolidin-3-yl]carbonyl]ethyl]amino]-5-cyano-1,2,3,4-tetrahydroquinoline

: 186355-58-8
methyl (2R,8S)-4-(benzyloxy)-6-(tert-butyloxycarbonyl)-8-hydroxy-2-methyl-1-oxo-2,3,6,7,8,9-hexahydro-1H-pyrrolo[3,2-f]quinoline-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 14 percent / LDA / tetrahydrofuran / 2 h / -78 °C

2.1: 70 percent / LDA / tetrahydrofuran / 6 h / -78 °C

3.1: 78 percent / LiOCH₃; CH₃OH / tetrahydrofuran / 0.5 h / 0 °C

4.1: 83 percent / TsOH*H₂O; water / tetrahydrofuran / 2 h / 0 °C

5.1: HCl / methanol / 1 h / 0 °C

5.2: 57 percent / tetrahydrofuran / 2 h / Heating

With hydrogenchloride; methanol; lithium methanolate; water; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1.1: Dieckmann condensation / 2.1: Isomerization / 3.1: methanolysis / 4.1: Hydrolysis / 5.1: deprotection / 5.2: alkoxycarbonylation;
DOI:10.1021/ja962431g