ethyl 4-(1-benzyl-2-oxo-Δ³-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

Base Information

• Chemical Name: ethyl 4-(1-benzyl-2-oxo-Δ³-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate
• CAS No.: 94405-13-7
• Molecular Formula: C₂₂H₂₁N₃O₄
• Molecular Weight: 391.426

Synonyms:ethyl 4-(1-benzyl-2-oxo-Δ³-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

Chemical Property of ethyl 4-(1-benzyl-2-oxo-Δ³-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

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Technology Process of ethyl 4-(1-benzyl-2-oxo-Δ³-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

There total 6 articles about ethyl 4-(1-benzyl-2-oxo-Δ³-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-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: 93.0%

ethyl 4-(1-benzyl-3-hydroxy-2-oxopyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate (94405-12-6) → ethyl 4-(1-benzyl-2-oxo-Δ3-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate (94405-13-7)

Guidance literature:

With hydrogenchloride; for 0.333333h; Ambient temperature;

DOI:10.1021/jo00204a001

Reference yield:

1-(1H-pyrrol-2-yl)butane-1,3-dione (22441-25-4) → ethyl 4-(1-benzyl-2-oxo-Δ3-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate (94405-13-7)

Guidance literature:

Multi-step reaction with 7 steps

1: hydroxylamine hydrochloride, Et₃N / methanol / 0.67 h / Heating

2: p-toluenesulfonic acid / methanol

3: 88 percent / 1,2-dichloro-ethane / 2 h / Heating

4: 99 percent / ethanol / 0.5 h

5: 87 percent / sodium acetate trihydrate, acetic acid, Br₂ / CH₂Cl₂ / 1.) 5 deg C, 5 min, 2.) RT, 20 min

7: 93 percent / conc. HCl / 0.33 h / Ambient temperature

With hydrogenchloride; hydroxylamine hydrochloride; bromine; sodium acetate; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo00204a001

Reference yield:

2-(3-methylisoxazol-5-yl)pyrrole (94405-06-8) → ethyl 4-(1-benzyl-2-oxo-Δ3-pyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate (94405-13-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / 1,2-dichloro-ethane / 2 h / Heating

2: 99 percent / ethanol / 0.5 h

3: 87 percent / sodium acetate trihydrate, acetic acid, Br₂ / CH₂Cl₂ / 1.) 5 deg C, 5 min, 2.) RT, 20 min

5: 93 percent / conc. HCl / 0.33 h / Ambient temperature

With hydrogenchloride; bromine; sodium acetate; acetic acid; In ethanol; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo00204a001

upstream raw materials:

ethyl 4-(1-benzyl-3-hydroxy-2-oxopyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

1-(1H-pyrrol-2-yl)butane-1,3-dione

2-(3-methylisoxazol-5-yl)pyrrole

ethyl 5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

Downstream raw materials:

ethyl 4-(1-benzyl-2-thioxopyrrolidin-3-yl)-5-(2-diazo-1,3-dioxobutyl)pyrrole-2-carboxylate

ethyl 4-(1-benzyl-2-oxopyrrolidin-3-yl)-5-(diazo-1,3-dioxobutyl)pyrrole-2-carboxylate

ethyl 4-(1-benzyl-2-thioxopyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

ethyl 4-(1-benzyl-2-oxopyrrolidin-3-yl)-5-(3-methylisoxazol-5-yl)pyrrole-2-carboxylate

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