ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate

Base Information

• Chemical Name: ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate
• CAS No.: 1443277-94-8
• Molecular Formula: C₂₁H₂₀N₂O₄
• Molecular Weight: 364.401
• Mol file: 1443277-94-8.mol

Synonyms:ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate

Chemical Property of ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate

There total 3 articles about ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-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: 90.0%

N-phenyl-maleimide (941-69-5) + ethyl N-benzylideneglycinate (40682-54-0) → ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate (1443277-94-8)

Guidance literature:

With C₃₂H₂₉FeN₂OP; silver(I) acetate; triethylamine; In toluene; at -20 ℃; for 12h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.05.003

Reference yield:

N-phenyl-maleimide (941-69-5) + ethyl N-benzylideneglycinate (40682-54-0) → ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate (1443277-94-8) + ethyl 4,6-dioxo-3,5-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Guidance literature:

With 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; water; silver fluoride; In toluene; at -20 ℃; for 10h; Solvent; Reagent/catalyst; Temperature; Time; Overall yield = 91%; Optical yield = 84 %ee; stereoselective reaction; Catalytic behavior;

DOI:10.1016/j.tet.2015.09.068

Reference yield:

N-phenyl-maleimide (941-69-5) + ethyl N-benzylideneglycinate (40682-54-0) → ethyl (1S,3R,3aS,6aR)-4,6-dioxo-3,5-diphenyloctahydropyrrole[3,4-c]pyrrole-1-carboxylate (1443277-94-8) + ethyl 4,6-dioxo-3,5-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate + (exo)-ethyl 4,6-dioxo-3,5-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Guidance literature:

With 2-((1R)-1-((tert-butylsulfinyl)amino)ethyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; silver fluoride; In ethanol; at -20 ℃; for 5h; Solvent; Overall yield = 80 %Spectr.; stereoselective reaction; Catalytic behavior;

DOI:10.1016/j.tet.2015.09.068

upstream raw materials:

N-phenyl-maleimide

ethyl N-benzylideneglycinate