(2S)-1-benzylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S)-1-benzylpyrrolidine-2-carboxylic acid
• CAS No.: 31795-93-4
• Molecular Formula: C12H15NO2
• Molecular Weight: 205.257
• Hs Code.: 2933990090
• European Community (EC) Number: 640-145-2
• DSSTox Substance ID: DTXSID20352538
• Nikkaji Number: J488.660G
• Mol file: 31795-93-4.mol

Synonyms:N-benzyl-L-proline

Chemical Property of (2S)-1-benzylpyrrolidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 2.76E-05mmHg at 25°C
• Melting Point: 168-171oC
• Refractive Index: 1.587
• Boiling Point: 343.1 °C at 760 mmHg
• PKA: 2.35±0.20(Predicted)
• Flash Point: 161.3 °C
• PSA: 40.54000
• Density: 1.205 g/cm³
• LogP: 1.67350
• Storage Temp.: Store at 0-5°C
• Solubility.: Acetone (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 205.110278721
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

N-Benzyl-(S)-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)CC2=CC=CC=C2)C(=O)O
• Uses: A reagent for the synthesis of optically pure a-amino-acids A reagent for the synthesis of optically pure α-amino-acids.

Technology Process of (2S)-1-benzylpyrrolidine-2-carboxylic acid

There total 13 articles about (2S)-1-benzylpyrrolidine-2-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: 93.2%

benzaldehyde (100-52-7) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-benzyl-L-proline (31795-93-4)

Guidance literature:

With hydrogen; Wilkinson's catalyst; In methanol; at 20 ℃; for 72h; under 37503 Torr;

DOI:10.1055/s-2004-830855

Reference yield: 92.0%

benzyl bromide (100-39-0) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-benzyl-L-proline (31795-93-4)

Guidance literature:

benzyl bromide; L-proline; With potassium hydroxide; In isopropyl alcohol; at 40 ℃;

With hydrogenchloride; In chloroform; water; isopropyl alcohol; at 20 ℃; for 12h; pH=4 - 5;

DOI:10.3390/molecules22101766

Reference yield: 91.0%

(S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate (83528-04-5) → N-benzyl-L-proline (31795-93-4)

Guidance literature:

With formic acid; potassium hydroxide; In ethanol; at 70 ℃; for 1h;

DOI:10.1002/adsc.201900686

upstream raw materials:

(S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate

benzyl chloride

L-proline

Fmoc-Pro-OH

Downstream raw materials:

N-benzyl-(S)-proline methyl ester

(1-benzylpyrrolidin-2-yl)phosphonic acid diethyl ester

Refernces

• 1、 Tararov, Vitali I.,Kadyrov, Renat,Fischer, Christine,B?rner, Armin. "Selective N-benzylation of amino acids under homogeneously catalyzed hydrogenation conditions". . p. 1961 - 1962. Retrieved 2004.
• 2、 Bonilla-Landa, Israel,Cuapio-Mu?oz, Ulises,Luna-Hernández, Axel,Reyes-Luna, Alfonso,Rodríguez-Hernández, Alfredo,Ibarra-Juarez, Arturo,Suarez-Mendez, Gabriel,Barrera-Méndez, Felipe,Caram-Salas, Nadia,Enríquez-Medrano, J. Francisco,Díaz De León, Ramón E.,Olivares-Romero, José Luis. "l -Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs". . p. 1455 - 1465. Retrieved 2021/02/16.
• 3、 Yakukhnov, Sergey A.,Ananikov, Valentine P.. "Catalytic Transfer Hydrodebenzylation with Low Palladium Loading". supporting information. p. 4781 - 4789. Retrieved 2019/09/16.