exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate

Base Information

• Chemical Name: exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate
• CAS No.: 75495-02-2
• Molecular Formula: C₂₁H₁₈N₂O₆S
• Molecular Weight: 426.45
• Mol file: 75495-02-2.mol

Synonyms:exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate

Chemical Property of exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate

There total 2 articles about exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate 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: 73.0%

N-phenyl-maleimide (941-69-5) + dimethyl 5-methyl-1H,3H-pyrrolo<1,2-c>thiazole-6,7-dicarboxylate 2-oxide (75475-92-2) → exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate (75495-02-2) + endo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate (75521-61-8)

Guidance literature:

With acetic anhydride; at 180 ℃; for 0.333333h; optical yield given as %de; Microwave irradiation;

DOI:10.1016/j.tet.2011.08.001

Reference yield:

dimethyl 5-methyl-1,3-dihydropyrrolo<1,2-c>thiazole-6,7-dicarboxylate (75475-91-1) → exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate (75495-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / N-chlorobenzotriazole / methanol / 1 h / -78 °C

2: 72 percent / acetic anhydride / 4 h / Heating

With N-chlorobenzotriazole; In methanol; acetic anhydride; 1: Oxidation / 2: Cycloaddition;

DOI:10.1016/S0040-4020(00)00956-X

Reference yield: 63.0%

exo-dimethyl 2,3,3a,4,9,9a-hexahydro-6-methyl-1,3-dioxo-2-phenyl-4,9-epithio-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate (75495-02-2) → dimethyl 2,3-dihydro-6-methyl-1,3-dioxo-2-phenyl-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate (75475-94-4)

Guidance literature:

With sodium methylate; In dichloromethane; for 2h;

DOI:10.1016/S0040-4020(00)00956-X

upstream raw materials:

N-phenyl-maleimide

dimethyl 5-methyl-1H,3H-pyrrolo<1,2-c>thiazole-6,7-dicarboxylate 2-oxide

dimethyl 5-methyl-1,3-dihydropyrrolo<1,2-c>thiazole-6,7-dicarboxylate

Downstream raw materials:

dimethyl 2,3-dihydro-6-methyl-1,3-dioxo-2-phenyl-1H-pyrrolo<3,4-f>indolizine-7,8-dicarboxylate