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

Base Information

• Chemical Name: methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-(trifluoromethylsulfonyl)-Δ²-pyrroline-2-carboxylate
• CAS No.: 1426680-66-1
• Molecular Formula: C₁₄H₂₀F₃NO₇S
• Molecular Weight: 403.377

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

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

Chemical Property:

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

There total 1 articles about methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-(trifluoromethylsulfonyl)-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:

3-amino-3-methylbutanoic acid (625-05-8) → methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-(trifluoromethylsulfonyl)-Δ2-pyrroline-2-carboxylate (1426680-66-1)

Guidance literature:

Multi-step reaction with 5 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

With dirhodium tetraacetate; 4-acetamidobenzenesulfonyl azide; potassium hexamethylsilazane; triethylamine; 1,1'-carbonyldiimidazole; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; toluene; acetonitrile;

DOI:10.1002/ejoc.201201420

Reference yield: 64.0%

methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-(trifluoromethylsulfonyl)-Δ2-pyrroline-2-carboxylate (1426680-66-1) + phenylboronic acid (98-80-6) → methyl N-(tert-butoxycarbonyl)-5,5-dimethyl-3-phenyl-Δ2-pyrroline-2-carboxylate (1426680-68-3)

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:

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

Guidance literature:

Multi-step reaction with 2 steps

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

2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; hydrogen; potassium carbonate; In methanol; toluene;

DOI:10.1002/ejoc.201201420

upstream raw materials:

3-amino-3-methylbutanoic acid

Downstream raw materials:

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

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