Methyl 1-benzylpyrrolidine-3-carboxylate

Base Information

• Chemical Name: Methyl 1-benzylpyrrolidine-3-carboxylate
• CAS No.: 17012-21-4
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.283
• Hs Code.: 2933990090
• European Community (EC) Number: 850-372-0
• Nikkaji Number: J46.450C
• Mol file: 17012-21-4.mol

Synonyms:17012-21-4;Methyl 1-benzylpyrrolidine-3-carboxylate;Methyl N-Benzyl-3-pyrrolidinecarboxylate;1-Benzyl-pyrrolidine-3-carboxylic acid methyl ester;MFCD04038678;METHYL 1-BENZYLLPYRROLIDINE-3-CARBOXYLATE;126344-02-3;METHYL N-BENZYLPYRROLIDINE-3-CARBOXYLATE;methyl 1-benzyl-3-pyrrolidinecarboxylate;3-PYRROLIDINECARBOXYLIC ACID, 1-(PHENYLMETHYL)-, METHYL ESTER;SCHEMBL1717074;GDWFCUOFVSNTTG-UHFFFAOYSA-N;BCP15617;CS-D0750;N-benzyl-3-carbomethoxy pyrrolidine;AKOS005215916;AC-1710;DS-1369;Methyl1-benzylpyrrolidine-3-carboxylate;PB20099;SB19987;Methyl 1-benzyl-3-pyrrolidylcarboxylate;SY004093;A3756;AM20030136;FT-0652874;FT-0658116;M2866;N-BENZYL-3-METHOXYCARBONYLPYRROLIDINE;(+/-) 1-Benzyl-3-methoxycarbonylpyrrolidine;EN300-54485;(+/-) Methyl 1-benzyl-3-pyrrolidylcarboxvlate;(+/-) methyl 1-benzyl-4-pyrrolidylcarboxylate;methyl 1-(phenylmethyl)pyrrolidine-3-carboxylate;1-benzylpyrrolidine-3-carboxylic acid methyl ester;A805547;W-206000;F1967-3059;methyl (+/-)-1-(phenylmethyl)-3-pyrrolidinecarboxylate;1-(phenylmethyl)-3-pyrrolidinecarboxylic acid methyl ester;(R/S)-1-Benzyl-pyrrolidin-3-yl carboxylic acid, methyl ester;(R/S)-1-Benzyl-pyrrolidin-3yl carboxylic acid, methyl ester

Chemical Property of Methyl 1-benzylpyrrolidine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.548
• Boiling Point: 292.096 °C at 760 mmHg
• PKA: 8.34±0.40(Predicted)
• Flash Point: 104.792 °C
• PSA: 29.54000
• Density: 1.121 g/cm³
• LogP: 1.61940
• Storage Temp.: 2-8°C
• Water Solubility.: Sparingly soluble in water.(0.26 g/L) (25°C),
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl 1-Benzylpyrrolidine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCN(C1)CC2=CC=CC=C2
• Uses: It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Technology Process of Methyl 1-benzylpyrrolidine-3-carboxylate

There total 14 articles about Methyl 1-benzylpyrrolidine-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: 100.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 1-benzylpyrrolidine-3-carboxylic acid methyl ester (17012-21-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2004.07.049

Reference yield: 91.0%

methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate (51535-00-3) → 1-benzylpyrrolidine-3-carboxylic acid methyl ester (17012-21-4)

Guidance literature:

With bis(2-chlorophenyl)borinic acid; phenylsilane; In neat (no solvent); at 20 ℃; for 12h; Sealed tube; Inert atmosphere;

DOI:10.1002/chem.201604802

Reference yield: 91.0%

N-benzyl-N-(butyloxymethyl)trimethylsilylmethylamine (93102-06-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 1-benzylpyrrolidine-3-carboxylic acid methyl ester (17012-21-4)

Guidance literature:

With cesium fluoride; trimethylsilyl iodide; In acetonitrile; at 60 ℃; for 15h;

DOI:10.1246/cl.1984.1117

upstream raw materials:

formaldehyd

acrylic acid n-butyl ester

N-benzylglycine

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

Downstream raw materials:

1-(Phenylmethyl)-3-pyrrolidinemethanol

pyrrolidine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

methyl 1-tert-butoxycarbonyl-3-pyrrolidinecarboxylate

Refernces

• 1、 Collins, Christopher J.,Lanz, Marc,Singaram, Bakthan. "Facile reduction of tertiary lactams to cyclic amines with 9- borabicyclo[3.3.1]nonane (9-BBN)". . p. 3673 - 3676. Retrieved 1999.
• 2、 Min, Rui,Wu, Weibin,Wang, Mingzhong,Tang, Lin,Chen, Dawei,Zhao, Huan,Zhang, Cunlong,Jiang, Yuyang. "Discovery of 2-(1-(3-(4-Chloroxyphenyl)-3-oxo-propyl)pyrrolidine-3-yl)-1H-benzo[d]imidazole-4-carboxamide: A Potent Poly(ADP-ribose) Polymerase (PARP) Inhibitor for Treatment of Cancer". . . Retrieved 2019/05/27.
• 3、 Chardon, Aurélien,Mohy El Dine, Tharwat,Legay, Rémi,De Paolis, Micha?l,Rouden, Jacques,Blanchet, Jér?me. "Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines". supporting information. p. 2005 - 2009. Retrieved 2017/02/19.