exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Base Information

Chemical Name:exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate
CAS No.:1356557-70-4
Molecular Formula:C₂₉H₂₉BrN₂O₆S
Molecular Weight:613.529
Hs Code.:

Synonyms:exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

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Chemical Property of exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

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Technology Process of exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

There total 6 articles about exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-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: 83.0%

: 1356557-57-7
C₂₉H₃₀N₂O₆S

: 1356557-70-4
exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Guidance literature:: With N-Bromosuccinimide; pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1002/ejoc.201101057

Reference yield:

: 7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8
(S)-tryptophan methyl ester hydrochloride

: 1356557-70-4
exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

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:

: 16874-03-6
N-[(phenylmethoxy)carbonyl]-L-tryptophan 1,1-dimethylethyl ester

: 1356557-70-4
exo-tert-butyl 1-benzyloxycarbonyl-3a-bromo-8-benzenesulfonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: dichloromethane / 2 h

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

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; In dichloromethane;
DOI:10.1002/ejoc.201101057