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

Base Information

Chemical Name:exo-methyl 1-benzyloxycarbonyl-3a-bromo-8-tert-butyloxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate
CAS No.:1356557-62-4
Molecular Formula:C₂₅H₂₇BrN₂O₆
Molecular Weight:531.403
Hs Code.:

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

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

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

There total 3 articles about exo-methyl 1-benzyloxycarbonyl-3a-bromo-8-tert-butyloxycarbonyl-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: 78.0%

: 643751-42-2
N-carbobenzyloxy-1-tert-butoxycarbonyl-L-tryptophan methyl ester

: 1356557-62-4
exo-methyl 1-benzyloxycarbonyl-3a-bromo-8-tert-butyloxycarbonyl-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

: 1356557-62-4
exo-methyl 1-benzyloxycarbonyl-3a-bromo-8-tert-butyloxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 15 h / 20 °C

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

With N-Bromosuccinimide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; triethylamine; sodium hydroxide; In dichloromethane;
DOI:10.1002/ejoc.201101057

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 1356557-62-4
exo-methyl 1-benzyloxycarbonyl-3a-bromo-8-tert-butyloxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane / 15 h / 20 °C

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

With N-Bromosuccinimide; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; triethylamine; sodium hydroxide; In dichloromethane;
DOI:10.1002/ejoc.201101057