(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

Base Information

Chemical Name:(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
CAS No.:1352575-49-5
Molecular Formula:C₃₄H₃₄N₄O₆
Molecular Weight:594.667
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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%

: 19005-93-7
1H-indol-2-ylcarboxaldehyde

: 1352575-48-4
(2R,3aS,8aS)-8-benzyl 1-tert-butyl 3a-bromo-2-(methylcarbamoyl)-3,3a-dihydropyrrolo[2,3-b]indole-1,8(2H,8aH)-dicarboxylate

: 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

Guidance literature:: With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; lithium bis[1,2-benzenediolato^(2-)-O,O'] borate; In dimethyl sulfoxide; at 20 ℃; for 6h; Reagent/catalyst; Solvent; Irradiation; Inert atmosphere;
DOI:10.1016/j.tet.2018.04.053

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

: 1352575-49-5
(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; tributyl-amine; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.201103145

Reference yield:

: 1352575-55-3
(R)-benzyl 3-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: N-Bromosuccinimide; pyridinium p-toluenesulfonate / dichloromethane / 12 h / 23 °C / Inert atmosphere

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

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

With N-Bromosuccinimide; tris(bipyridine)ruthenium(II) dichloride hexahydrate; tributyl-amine; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.201103145