(3S,4R)-1-Benzyl-4-(4-methylphenyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3S,4R)-1-Benzyl-4-(4-methylphenyl)pyrrolidine-3-carboxylic acid
• CAS No.: 80896-75-9
• Molecular Formula: C₁₉H₂₁NO₂
• Molecular Weight: 295.381
• Hs Code.: 2933990090
• Nikkaji Number: J2.035.328G
• Mol file: 80896-75-9.mol

Synonyms:1820581-27-8;(3S,4R)-1-BENZYL-4-(4-METHYLPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID;trans-1-Benzyl-4-(p-tolyl)pyrrolidine-3-carboxylic acid;SCHEMBL9925995;EN300-225351;EN300-735860;A840004;(3S,4R)-1-BENZYL-4-(4-METHYLPHENYL)PYRROLIDINE-3-CARBOXYLICACID;rac-(3R,4S)-1-benzyl-4-(4-methylphenyl)pyrrolidine-3-carboxylic acid

Chemical Property of (3S,4R)-1-Benzyl-4-(4-methylphenyl)pyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 463.847°C at 760 mmHg
• Flash Point: 234.326°C
• PSA: 40.54000
• Density: 1.178g/cm³
• LogP: 3.23310
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 295.157228913
• Heavy Atom Count: 22
• Complexity: 370

Purity/Quality:

98% ^*data from raw suppliers

trans-1-Benzyl-4-(p-tolyl)pyrrolidine-3-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2CN(CC2C(=O)O)CC3=CC=CC=C3
• Isomeric SMILES: CC1=CC=C(C=C1)[C@@H]2CN(C[C@H]2C(=O)O)CC3=CC=CC=C3

Technology Process of (3S,4R)-1-Benzyl-4-(4-methylphenyl)pyrrolidine-3-carboxylic acid

There total 15 articles about (3S,4R)-1-Benzyl-4-(4-methylphenyl)pyrrolidine-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: 100.0%

(3SR,4SR)ethyl 1-benzyl-4-(p-tolyl)pyrrolidine-3-carboxylate → trans-1-benzyl-4-(p-tolyl)pyrrolidine-3-carboxylic acid (80896-75-9)

Guidance literature:

With barium dihydroxide; In ethanol; for 15h; Heating;

DOI:10.1002/hlca.19810640727

Reference yield:

ethyl (Z)-3-(4-methylphenyl)-2-propenoate (20511-20-0,24393-49-5,97585-04-1) → (3S,4S)-1-Benzyl-4-p-tolyl-pyrrolidine-3-carboxylic acid (80896-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂

2: aq. HCl

With hydrogenchloride; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2006.04.070

Reference yield:

methyl 1-benzyl-3,4-trans-4-p-tolylpyrrolidine-3-carboxylate trifluoroacetate → trans-1-benzyl-4-(p-tolyl)pyrrolidine-3-carboxylic acid (80896-75-9)

Guidance literature:

methyl 1-benzyl-3,4-trans-4-p-tolylpyrrolidine-3-carboxylate trifluoroacetate; With lithium hydroxide; water; In tetrahydrofuran; at 80 ℃; for 2h;

With acetic acid; In tetrahydrofuran; water;

upstream raw materials:

4-methylphenylboronic acid

tert-butyl 1-(phenylmethyl)-2,5-dihydropyrrole-3-carboxylate

4-methyl-benzaldehyde

ethyl (Z)-3-(4-methylphenyl)-2-propenoate

Refernces

• 1、 Huck, Bayard R.,Llamas, Luis,Robarge, Michael J.,Dent, Thomas C.,Song, Jianping,Hodnick, William F.,Crumrine, Chris,Stricker-Krongrad, Alain,Harrington, John,Brunden, Kurt R.,Bennani, Youssef L.. "The design and synthesis of a tricyclic single-nitrogen scaffold that serves as a 5-HT2C receptor agonist". . p. 4130 - 4134. Retrieved 2007/10/03.
• 2、 Belyk, Kevin M.,Beguin, Charlotte D.,Palucki, Michael,Grinberg, Nelu,DaSilva, Jimmy,Askin, David,Yasuda, Nobuyoshi. "A rapid catalytic asymmetric synthesis of 1,3,4-trisubstituted pyrrolidines". . p. 3265 - 3268. Retrieved 2007/10/03.