1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid

Base Information

• Chemical Name: 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid
• CAS No.: 1229236-32-1
• Molecular Formula: C₁₈H₁₆ClNO₂
• Molecular Weight: 313.784
• Mol file: 1229236-32-1.mol

Synonyms:1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid

Chemical Property of 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid

There total 3 articles about 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid 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: 79.0%

ethyl 3-(4-chlorophenyl)propiolate (20026-96-4) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (1229236-32-1)

Guidance literature:

ethyl 3-(4-chlorophenyl)propiolate; N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 24h; Cooling with water;

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 67h;

With hydrogenchloride; In water; at 5 ℃; for 1h; pH=1.5;

Reference yield: 76.0%

3-(4-chlorophenyl)-2-propionic acid ethyl ester (1030828-84-2) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (1229236-32-1)

Guidance literature:

3-(4-chlorophenyl)-2-propionic acid ethyl ester; N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; With trifluoroacetic acid; In dichloromethane; at 0 - 25 ℃;

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 72h;

Reference yield:

1-Chloro-4-iodobenzene (637-87-6) → 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (1229236-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: caesium carbonate / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 41.33 h / 35 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 25.5 h / 20 °C / Cooling

2.2: 67 h / 20 °C

2.3: 5 °C / pH 1.5

With caesium carbonate; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; dichloromethane;

upstream raw materials:

ethyl 3-(4-chlorophenyl)propiolate

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

3-(4-chlorophenyl)-2-propionic acid ethyl ester

1-Chloro-4-iodobenzene

Downstream raw materials:

[(3S,4R)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-amine

[(3S,4R)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

[(3S,4R)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-carbamic acid methyl ester

(3S,4R)-1-benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid amide