endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Base Information

• Chemical Name: endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate
• CAS No.: 1356557-72-6
• Molecular Formula: C₂₃H₂₅BrN₂O₆S
• Molecular Weight: 537.431
• Mol file: 1356557-72-6.mol

Synonyms:

Chemical Property of endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

There total 5 articles about endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-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:

C23H26N2O6S (1356557-58-8) → endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate (1356557-72-6) + exo-tert-butyl 8-benzenesulfonyl-3a-bromo-1-methoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate (1356557-73-7)

Guidance literature:

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 4h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201101057

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate (1356557-72-6) + exo-tert-butyl 8-benzenesulfonyl-3a-bromo-1-methoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate (1356557-73-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 2 h / 20 °C

2.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 20 °C

2.2: pH 5

3.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / acetonitrile / 5 h

3.2: 2 h / 50 °C

4.1: dichloromethane / 2 h

5.1: N-Bromosuccinimide; pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; N-benzyl-N,N,N-triethylammonium chloride; water; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201101057

Reference yield:

N-(methoxycarbonyl)-L-tryptophan methyl ester (66377-68-2,79631-04-2,58635-46-4) → endo-(2S,3aS,8aS)-tert-butyl 3a-bromo-1-methoxycarbonyl-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate (1356557-72-6) + exo-tert-butyl 8-benzenesulfonyl-3a-bromo-1-methoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate (1356557-73-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; lithium hydroxide / tetrahydrofuran / 3 h / 20 °C

1.2: pH 5

2.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate / acetonitrile / 5 h

2.2: 2 h / 50 °C

3.1: dichloromethane / 2 h

4.1: N-Bromosuccinimide; pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; N-benzyl-N,N,N-triethylammonium chloride; water; pyridinium p-toluenesulfonate; potassium carbonate; lithium hydroxide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201101057

upstream raw materials:

C₂₃H₂₆N₂O₆S

N^b-methoxycarbonyl-L-tryptophan tert-butyl ester

C₂₃H₂₆N₂O₆S

(S)-tryptophan methyl ester hydrochloride