(2S,3R)-Methyl 2-(4-methoxyphenyl)pyrrolidine-3-carboxylate

Base Information

• Chemical Name: (2S,3R)-Methyl 2-(4-methoxyphenyl)pyrrolidine-3-carboxylate
• CAS No.: 748777-12-0
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.283
• Mol file: 748777-12-0.mol

Synonyms:LogP

Chemical Property of (2S,3R)-Methyl 2-(4-methoxyphenyl)pyrrolidine-3-carboxylate

Chemical Property:

• Vapor Pressure: 7.36E-05mmHg at 25°C
• Refractive Index: 1.518
• Boiling Point: 342.8°C at 760 mmHg
• PKA: 9.11±0.10(Predicted)
• Flash Point: 161.1°C
• PSA: 47.56000
• Density: 1.117g/cm³
• LogP: 1.84760
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

cis-Methyl2-(4-methoxyphenyl)pyrrolidine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3R)-Methyl 2-(4-methoxyphenyl)pyrrolidine-3-carboxylate

There total 5 articles about (2S,3R)-Methyl 2-(4-methoxyphenyl)pyrrolidine-3-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: 92.0%

C14H16N2O3 → (2S,3R)-2-(4-Methoxy-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (748777-12-0)

Guidance literature:

C₁₄H₁₆N₂O₃; With borane-THF; In tetrahydrofuran; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 2.5h; Inert atmosphere;

With palladium 10% on activated carbon; In methanol; Inert atmosphere;

DOI:10.1002/anie.201500961

Reference yield: 76.0%

4-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester → (2S,3R)-2-(4-Methoxy-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (748777-12-0)

Guidance literature:

With titanium tetrachloride; triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2004.06.080

Reference yield:

methyl 4-aminobutyrate (3251-07-8) → (2S,3R)-2-(4-Methoxy-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (748777-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; 4 Angstroem MS / CH₂Cl₂ / 48 h / 20 °C

2: 76 percent / triethylamine; TiCl₄ / CH₂Cl₂ / 3 h / 20 °C

With 4 Angstroem MS; titanium tetrachloride; triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2004.06.080

upstream raw materials:

methyl 4-aminobutyrate

4-methoxy-benzaldehyde

Refernces

• 1、 Suresh, Surisetti,Periasamy, Mariappan. "Synthesis of cis-2-aryl-3-pyrrolidine carboxylic esters via diastereoselective cyclization of γ-imino esters using a TiCl 4/Et3N reagent system". . p. 6291 - 6293. Retrieved 2007/10/03.