methyl (2S,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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.:186355-92-0
Molecular Formula:C₃₄H₃₅N₃O₁₁S
Molecular Weight:693.731
Hs Code.:

methyl (2S,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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 25 articles about methyl (2S,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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: 91.0%

: 124-63-0
methanesulfonyl chloride

: 186355-90-8
methyl (2S,8R)-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

: 186355-92-0
methyl (2S,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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 pyridine; at 0 ℃; for 1h;
DOI:10.1021/ja953777e

Reference yield:

: 25945-96-4
2-benzyloxy-4-nitro-phenylamine

: 186355-92-0
methyl (2S,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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 20 steps

1: 100 percent / NBS / acetonitrile / 2 h / 25 °C

2: 95 percent / dimethylformamide / 16 h / Heating

3: 100 percent / Al(Hg) / diethyl ether; aq. ethanol / 2 h / 0 - 25 °C

4: 96 percent / K₂CO₃, DMAP / tetrahydrofuran / 16 h / 25 °C

5: 84 percent / Pb(OAc)4 / CHCl₃ / 4 h / 0 - 25 °C

6: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

7: (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃, CH₃SO₂NH₂ / tetrahydrofuran; H₂O / 16 h

8: 1.) Bu₂SnO, 2.) Et₃N / 1.) toluene, THF, reflux, 6 h, 2.) 25 deg C, 12 h

9: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

10: NaH / tetrahydrofuran / 2 h / 0 °C

11: NH₂NH₂, EtOH / 20 h / 140 °C

12: 95 percent / DMAP / tetrahydrofuran / 4 h / Heating

13: 93 percent / TFA / CH₂Cl₂ / 3 h / -30 - 0 °C

14: NaH / dimethylformamide / 1 h / 0 °C

15: LDA / tetrahydrofuran

16: MeOLi / tetrahydrofuran / 0.5 h / 0 °C

17: 80 percent / aq. TsOH / tetrahydrofuran / 3 h / 0 °C

18: 4 M HCl / methanol / 1 h / 0 °C

19: EDCI / dimethylformamide / 4 h / 25 °C

20: 91 percent / pyridine / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; hydrogenchloride; dmap; aluminum amalgam; N-Bromosuccinimide; osmium(VIII) oxide; (DHQ)2-PHAL; ethanol; methanesulfonamide; boron trifluoride diethyl etherate; lithium methanolate; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; potassium hexacyanoferrate(III); hydrazine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja953777e

Reference yield:

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

: 186355-92-0
methyl (2S,8R)-4-(benzyloxy)-8-[(methanesulfonyl)oxy]-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: EDCI / dimethylformamide / 4 h / 25 °C

2: 91 percent / pyridine / 1 h / 0 °C

With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide;
DOI:10.1021/ja953777e