3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical

Base Information

• Chemical Name: 3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical
• CAS No.: 149473-06-3
• Molecular Formula: C₁₃H₂₂NO₃
• Molecular Weight: 240.323
• Mol file: 149473-06-3.mol

Synonyms:3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical

Chemical Property of 3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical

There total 1 articles about 3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical 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: 72.0%

(2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol (55738-75-5) + Triethyl orthoacetate (78-39-7) → 3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical (149473-06-3)

Guidance literature:

With propionic acid; at 140 ℃; for 8h;

DOI:10.1055/s-1993-25870

Reference yield:

3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical (149473-06-3) → 3-<(4-azido-N-phthalimido)ethyl>-4-methanethiosulfonylmethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy radical

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / NaBH₄ / 2-methyl-propan-2-ol; methanol

2: Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: LiBr / acetone / 1 h / Heating

4: 35 percent / K₂CO₃, KOH, 18-crown-6 / dioxane / 18 h / Heating

5: 1.) ascorbinic acid, 2.) Et₃N / 1.) dioxane, H₂O, 40 deg C, 15 min, 2.) CHCl₃, 0 deg C, 1 h

6: 56 percent / NBS, benzoylperoxide / CCl₄ / 14 h / Heating; var. reag.: 1,3-dibromo-5,5-dimethylhydantoine

7: 28 percent / NaOMe / methanol; tetrahydrofuran / 0.5 h / Ambient temperature; spontaneous oxidation

8: 66 percent / dioxane; H₂O / 0.5 h / Heating

With potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; Perbenzoic acid; 18-crown-6 ether; sodium methylate; potassium carbonate; triethylamine; lithium bromide; ascorbic acid; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1055/s-1994-25641

Reference yield:

3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical (149473-06-3) → 1-acetoxy-4-ethoxycarbonyl-2,5-dihydro-2,2,5,5-tetramethyl-4-methanethiosulfonylmethyl-1H-pyrrole (149473-20-1)

Guidance literature:

Multi-step reaction with 4 steps

1: ascorbic acid / dioxane; H₂O / 1 h / 40 °C

2: Et₃N / < 10 deg C, 1 h

3: 67 percent / NBS, benzoyl peroxide / CCl₄ / 6 h / Heating

4: 54 percent / ethanol / 1 h / Heating

With N-Bromosuccinimide; Perbenzoic acid; triethylamine; ascorbic acid; In 1,4-dioxane; tetrachloromethane; ethanol; water;

DOI:10.1055/s-1993-25870

upstream raw materials:

(2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol

Triethyl orthoacetate

Downstream raw materials:

1-acetoxy-4-ethoxycarbonyl-2,5-dihydro-2,2,5,5-tetramethyl-4-methanethiosulfonylmethyl-1H-pyrrole