(2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Base Information

• Chemical Name: (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS No.: 1001565-97-4
• Molecular Formula: C₂₃H₂₅BrN₂O₆S
• Molecular Weight: 537.431
• Mol file: 1001565-97-4.mol

Synonyms:(2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property of (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 2 articles about (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 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: 84.0%

(R)-3-(1-benzenesulfonyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (1001565-88-3) → (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1001565-97-4)

Guidance literature:

With magnesium bromide; In water; acetonitrile; at 20 ℃; for 2h; Electrolysis;

DOI:10.1039/c9cc09276e

Reference yield: 78.7%

(R)-3-(1-benzenesulfonyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester (1001565-88-3) → (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1001565-97-4) + C23H25BrN2O6S

Guidance literature:

With N-Bromosuccinimide; pyridinium p-toluenesulfonate; In dichloromethane; at 23 ℃; for 1.5h; Overall yield = 99.6 %; Overall yield = 11.6 g; Inert atmosphere;

DOI:10.1021/jacs.6b04072

Reference yield: 98.5%

indole (120-72-9) + (2R,3aS,8aS)-8-benzenesulfonyl-3a-bromo-2,3,3a,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (1001565-97-4) → (2S,3aS,8aS)-1-tert-butyl 2-methyl 3a-(1H-indol-3-yl)-8-(phenylsulfonyl)-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indole-1,2(2H)-dicarboxylate

Guidance literature:

With triethyl borane; potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 2h;

upstream raw materials:

(R)-3-(1-benzenesulfonyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester