ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

Base Information

• Chemical Name: ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate
• CAS No.: 1596355-35-9
• Molecular Formula: C₂₂H₁₉BrN₂O₅
• Molecular Weight: 471.307
• Mol file: 1596355-35-9.mol

Synonyms:ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

Chemical Property of ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

There total 2 articles about ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-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:

N-phenyl-maleimide (941-69-5) + C12H12BrNO3 (861335-71-9) → ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate (1596355-35-9) + ethyl (3R)-5-bromo-3-[(3R)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate + ethyl 5-bromo-3-[2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

Guidance literature:

With cinchonidine; In chloroform; at -35 ℃; for 48h; Overall yield = 91%; enantioselective reaction;

DOI:10.1016/j.tet.2014.03.065

Reference yield:

5-bromo-1-methyl-1,3-dihydro-indol-2-one (20870-90-0) → ethyl (3S)-5-bromo-3-[(3S)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate (1596355-35-9) + ethyl (3R)-5-bromo-3-[(3R)-2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate + ethyl 5-bromo-3-[2,5-dioxo-1-phenylpyrrolidin-3-yl]-1-methyl-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: sodium ethanolate / ethanol / 15 h / Inert atmosphere; Reflux

2: cinchonidine / chloroform / 48 h / -35 °C

With sodium ethanolate; cinchonidine; In ethanol; chloroform;

DOI:10.1016/j.tet.2014.03.065

upstream raw materials:

N-phenyl-maleimide

C₁₂H₁₂BrNO₃

5-bromo-1-methyl-1,3-dihydro-indol-2-one