methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

Base Information

Chemical Name:methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate
CAS No.:1426680-68-3
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ<sup>2</sup>-pyrroline-2-carboxylate

Synonyms:methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

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Chemical Property of methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

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Technology Process of methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

There total 8 articles about methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-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: 64.0%

: 1426680-66-1
methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-(trifluoromethylsulfonyl)-Δ²-pyrroline-2-carboxylate

: 98-80-6
phenylboronic acid

: 1426680-68-3
methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In methanol; toluene; at 80 ℃; for 1h;
DOI:10.1002/ejoc.201201420

Reference yield:

: 625-05-8
3-amino-3-methylbutanoic acid

: 1426680-68-3
methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium hydroxide / 1,4-dioxane; water / 36 h

2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

3.1: 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 2 h / 20 °C / Inert atmosphere

4.1: dirhodium tetraacetate / toluene / 0.67 h / 85 - 90 °C / Inert atmosphere

5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / 20 °C

5.2: 4 h / 20 °C

6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / toluene; methanol / 1 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dirhodium tetraacetate; 4-acetamidobenzenesulfonyl azide; potassium hexamethylsilazane; potassium carbonate; triethylamine; 1,1'-carbonyldiimidazole; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; toluene; acetonitrile;
DOI:10.1002/ejoc.201201420

Reference yield:

: 129765-95-3
3-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid

: 1426680-68-3
methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ²-pyrroline-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 18 h / 20 °C / Inert atmosphere

2.1: 4-acetamidobenzenesulfonyl azide; triethylamine / acetonitrile / 2 h / 20 °C / Inert atmosphere

3.1: dirhodium tetraacetate / toluene / 0.67 h / 85 - 90 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.67 h / 20 °C

4.2: 4 h / 20 °C

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / toluene; methanol / 1 h / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dirhodium tetraacetate; 4-acetamidobenzenesulfonyl azide; potassium hexamethylsilazane; potassium carbonate; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; toluene; acetonitrile;
DOI:10.1002/ejoc.201201420