methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate

Base Information

• Chemical Name: methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate
• CAS No.: 128243-98-1
• Molecular Formula: C₁₅H₁₆N₂O₃
• Molecular Weight: 272.304
• Mol file: 128243-98-1.mol

Synonyms:methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate

Chemical Property of methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate

There total 6 articles about methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-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: 76.4%

methyl 1-benzoylpyrrolidine-2-carboxylate (114051-14-8) + cyanomethyl bromide (590-17-0) → methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate (128243-98-1)

Guidance literature:

methyl 1-benzoylpyrrolidine-2-carboxylate; With lithium diisopropyl amide; In tetrahydrofuran; hexanes; at -77 ℃; for 3h; Inert atmosphere;

cyanomethyl bromide; In tetrahydrofuran; hexanes; at -77 - 20 ℃;

Reference yield:

N-benzoyl-L-proline methyl ester (5493-38-9) + cyanomethyl bromide (590-17-0) → methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate (128243-98-1)

Guidance literature:

N-benzoyl-L-proline methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

cyanomethyl bromide; In tetrahydrofuran; at 15 ℃; for 18h;

Reference yield:

N-(benzoyl)-L-proline (5874-58-8) → methyl 1-benzoyl-2-(nitrilomethyl)pyrrolidine-2-carboxylate (128243-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / thionyl chloride / 1.) 0 deg C, 1 h, 2.) RT, overnight

2: 1.) LDA, N,N,N',N'-tetramethylenediamine / 1.) THF, hexanes, -75 deg C, 10 min, 2.) a.) -78 deg C, 1 h, b.) from -78 deg C to 0 deg C

With thionyl chloride; N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide;

DOI:10.1021/jm00170a035

upstream raw materials:

N-benzoyl-L-proline methyl ester

chloroacetonitrile

N-(benzoyl)-L-proline

methyl 1-benzoylpyrrolidine-2-carboxylate

Downstream raw materials:

2-(2-Amino-ethyl)-1-benzoyl-pyrrolidine-2-carboxylic acid methyl ester

1-(phenylmethyl)-1,7-diazaspiro<4.4>nonane

1-benzoyl-1,7-diazaspiro<4.4>nonan-6-one