methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Base Information

• Chemical Name: methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• CAS No.: 939799-29-8
• Molecular Formula: C₂₁H₂₀N₂O₄
• Molecular Weight: 364.401
• Mol file: 939799-29-8.mol

Synonyms:methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Chemical Property of methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

There total 3 articles about methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[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: 92.0%

N-phenyl-maleimide (941-69-5) + [(4-methyl-benzylidene)-amino]-acetic acid methyl ester → methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (939799-29-8)

Guidance literature:

With copper(I) trifluoromethanesulfonate * 1/2 toluene; (R(P))-2-(tert-butylsulfenyl)-1-(diphenylphosphino)ferrocene; potassium hexamethylsilazane; In tetrahydrofuran; at -40 ℃; for 18h; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.3762/bjoc.12.140

Reference yield:

N-phenyl-maleimide (941-69-5) + [(4-methyl-benzylidene)-amino]-acetic acid methyl ester → methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (939799-29-8) + methyl (1R,3S,3aR,6aS)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (1169983-13-4)

Guidance literature:

With copper(I) trifluoromethanesulfonate * 1/2 toluene; (R(P))-2-(tert-butylsulfenyl)-1-(diphenylphosphino)ferrocene; potassium hexamethylsilazane; In tetrahydrofuran; at -40 ℃; for 48h; Overall yield = 91 %; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.3762/bjoc.12.140

Reference yield:

N-phenyl-maleimide (941-69-5) + (E)-[(4-methyl-benzylidene)-amino]-acetic acid methyl ester (76862-10-7) → methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (939799-29-8) + methyl (1R,3S,3aR,6aS)-4,6-dioxo-3-(p-methylphenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate (1169983-13-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; chiral 1,1'-binaphthyl-2,2'-diamine-based nickel(II) complex; In dichloromethane; at 15 ℃; for 24h; Title compound not separated from byproducts.;

DOI:10.1021/jo701561d

upstream raw materials:

N-phenyl-maleimide

(E)-[(4-methyl-benzylidene)-amino]-acetic acid methyl ester