1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

Base Information

Chemical Name:1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate
CAS No.:1369969-31-2
Molecular Formula:C₂₉H₃₆N₂O₇
Molecular Weight:524.614
Hs Code.:

Synonyms:1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

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Chemical Property of 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

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Technology Process of 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

There total 3 articles about 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate 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: 75.0%

: 696-62-8
para-iodoanisole

: 1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-chloro-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

: 1369969-31-2
1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

Guidance literature:: With pyridine; bis(acetylacetonate)nickel(II); water; magnesium chloride; zinc; In N,N-dimethyl acetamide; at 25 ℃; for 12h; Inert atmosphere; Schlenk technique;
DOI:10.1021/jacs.8b09473

Reference yield: 72.0%

: 1064604-21-2
methyl (2S,3aR,8aR)-[3a-bromo-(1,2,3,3a,8,8a)-hexahydropyrrolo[2,3-b]indole-1,8-di-tertbutoxycarbonyl]-2-carboxylate

: 100-66-3
methoxybenzene

: 1369969-31-2
1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

Guidance literature:: With silver tetrafluoroborate; caesium carbonate; In dichloromethane; at -78 ℃; for 10h; stereoselective reaction; Inert atmosphere;
DOI:10.1039/c2ob00014h

Reference yield:

: 96238-68-5
tert-butyl (+)-(S)-3-[2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl]-1H-indole-1-carboxylate

: 1369969-31-2
1,8-di-tert-butyl 2-methyl (2S,3aR,8aR)-3a-(4-methoxyphenyl)-2,3,3a,8a-tetrahydropyrrolo[2,3-b]indole-1,2,8-tricarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate; N-Bromosuccinimide / dichloromethane / 4 h / 0 °C / Inert atmosphere

2: caesium carbonate; silver tetrafluoroborate / dichloromethane / 10 h / -78 °C / Inert atmosphere

With N-Bromosuccinimide; silver tetrafluoroborate; pyridinium p-toluenesulfonate; caesium carbonate; In dichloromethane; 2: |Friedel-Crafts Alkylation;
DOI:10.1039/c2ob00014h