(2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate
• CAS No.: 31560-20-0
• Molecular Formula: C13H15 N O4
• Molecular Weight: 249.266
• Hs Code.: 2933990090
• European Community (EC) Number: 411-020-8,601-739-7,608-637-1
• DSSTox Substance ID: DTXSID90953536
• Nikkaji Number: J775.977K
• Wikidata: Q82932416
• Mol file: 31560-20-0.mol

Synonyms:(2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate;31560-20-0;120806-96-4;trans-1-benzoyl-4-hydroxyl-L-proline methyl ester;methyl (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylate;trans-1-Benzoyl-4-hydroxy-L-proline methyl ester;N-Benzoylhydroxy-L-prolinmethylester;SCHEMBL2059306;AMY2400;DTXSID90953536;Methyl 1-benzoyl-4-hydroxyprolinate;AKOS000278449;AC-22525;SQ 29,242;1-Benzoyl-4beta-hydroxy-L-proline methyl ester;EC 411-020-8;(trans)-1-benzoyl-4-hydroxy-L-proline methyl ester;(trans)-1-Benzoyl-4-hydroxy-L-proline, methyl ester;(2S,4R)-1-benzoyl-4-hydroxy-pyrrolydin-2-carboxylic acid methyl ester

Chemical Property of (2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.31E-07mmHg at 25°C
• Refractive Index: 1.585
• Boiling Point: 414.3oC at 760 mmHg
• Flash Point: 204.4oC
• PSA: 66.84000
• Density: 1.302g/cm3
• LogP: 0.37290
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 325

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-Methyl1-benzoyl-4-hydroxypyrrolidine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(CN1C(=O)C2=CC=CC=C2)O
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H](CN1C(=O)C2=CC=CC=C2)O

Technology Process of (2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-2-carboxylate

There total 6 articles about (2S,4R)-Methyl 1-benzoyl-4-hydroxypyrrolidine-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: 98.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + benzoyl chloride (98-88-4) → (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (31560-20-0,120806-96-4)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c4ob02002b

Reference yield: 92.0%

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) + benzoyl chloride (98-88-4) → (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (31560-20-0,120806-96-4)

Guidance literature:

With sodium carbonate; at 0 ℃; for 4h;

DOI:10.1248/cpb.43.1302

Reference yield:

methyl (2S,4R)-1-benzoyl-4-(benzyloxy)pyrrolidine-2-carboxylate → (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (31560-20-0,120806-96-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; water; at 20 ℃; for 2h;

upstream raw materials:

(R)-4-hydroxy-L-proline ethyl ester

benzoyl chloride

L-4-hydroxyproline methyl ester hydrochloride

4R-4-hydroxyproline

Downstream raw materials:

trans-N-benzoyl-4-mesyloxy-L-proline methyl ester

fosinopril

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid

trans-4-phenyl-L-proline

Refernces

• 1、 Zanato, Chiara,Watson, Sonia,Bewick, Guy S.,Harrison, William T. A.,Zanda, Matteo. "Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands". supporting information. p. 9638 - 9643. Retrieved 2015/02/19.
• 2、 Arakawa, Yasushi,Ohnishi, Masafumi,Yoshimura, Norikazu,Yoshifuji, Shigeyuki. "Synthetic study of optically active 3-azabicyclo[3.3.0]octane-2,6,8- tricarboxylic acid". . p. 1015 - 1020. Retrieved 2007/10/03.