(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

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Chemical Name:(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate
CAS No.:1352575-53-1
Molecular Formula:C₃₈H₂₈N₄O₇
Molecular Weight:652.663
Hs Code.:

(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

Synonyms:(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

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Chemical Property of (5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

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Technology Process of (5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

There total 9 articles about (5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-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: 49.0%

: 1352575-54-2
(3aR,8aS)-benzyl 3a-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-8(8aH)-carboxylate

: 4755-77-5
Ethyl oxalyl chloride

: 1352575-53-1
(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

Guidance literature:: With triethylamine; In toluene; at 150 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;
DOI:10.1002/anie.201103145

Reference yield:

: 1352575-47-3
(2R,3aS,8aS)-8-benzyl 1-tert-butyl 2-methyl 3a-bromo-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate

: 1352575-53-1
(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran; water / 96 h / 23 °C / Inert atmosphere

2.1: tris(bipyridine)ruthenium(II) dichloride hexahydrate; tributyl-amine / N,N-dimethyl-formamide / 12 h / 30 °C / Inert atmosphere; Irradiation

3.1: Wilkinson's catalyst / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C / Inert atmosphere

4.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 5 h / 23 °C / Inert atmosphere

5.1: trimethylsilyl iodide / acetonitrile / 0.5 h / 0 °C / Inert atmosphere

6.1: N-Bromosuccinimide / dichloromethane / 0.5 h / 23 °C / Inert atmosphere

6.2: 0.5 h / Inert atmosphere

7.1: triethylamine / toluene / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation

With N-Bromosuccinimide; Wilkinson's catalyst; tris(bipyridine)ruthenium(II) dichloride hexahydrate; tributyl-amine; trimethylsilyl iodide; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; sodium hydroxide; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/anie.201103145

Reference yield:

: 1352575-49-5
(2R,3aR,8aS)-8-benzyl 1-tert-butyl 3a-(2-formyl-1H-indol-3-yl)-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

: 1352575-53-1
(5aS,10bR)-benzyl 10b-(1-((benzyloxy)carbonyl)-1H-indol-3-yl)-2-methyl-1,3,4-trioxo-3,4,5a,10b-tetrahydro-1H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-6(2H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Wilkinson's catalyst / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / 140 °C / Inert atmosphere

2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 5 h / 23 °C / Inert atmosphere

3.1: trimethylsilyl iodide / acetonitrile / 0.5 h / 0 °C / Inert atmosphere

4.1: N-Bromosuccinimide / dichloromethane / 0.5 h / 23 °C / Inert atmosphere

4.2: 0.5 h / Inert atmosphere

5.1: triethylamine / toluene / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation

With N-Bromosuccinimide; Wilkinson's catalyst; trimethylsilyl iodide; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; toluene; acetonitrile;
DOI:10.1002/anie.201103145