Methyl D-prolinate

Base Information

• Chemical Name: Methyl D-prolinate
• CAS No.: 43041-12-9
• Molecular Formula: C6H11 N O2
• Molecular Weight: 129.159
• Hs Code.: 2933990090
• European Community (EC) Number: 256-057-9
• UNII: EON208T642
• DSSTox Substance ID: DTXSID401314597
• Nikkaji Number: J269.457C
• Wikidata: Q27277272
• Mol file: 43041-12-9.mol

Synonyms:43041-12-9;Methyl D-prolinate;(R)-methyl pyrrolidine-2-carboxylate;D-Proline, methyl ester;methyl (2R)-pyrrolidine-2-carboxylate;d-proline methyl ester;(R)-proline methyl ester;UNII-EON208T642;EON208T642;EINECS 256-057-9;MFCD06656665;(R)-pyrrolidine-2-carboxylic acid methyl ester;d-proline methylester;(2R)-proline methylester;SCHEMBL708271;METHYL PROLINE, (R)-;METHYL PROLINE, (+)-;DTXSID401314597;(r)-methylpyrrolidine-2-carboxylate;AKOS015850884;(R)-2-(METHOXYCARBONYL)PYRROLIDINE;CS-0059199;METHYL (R)-PYRROLIDINE-2-CARBOXYLATE;D82335;EN300-395314;A826118;Q27277272;(R)-pyrrolidine-2-carboxylic acid methyl ester, AldrichCPR

Chemical Property of Methyl D-prolinate

Chemical Property:

• Vapor Pressure: 1.51mmHg at 25°C
• Boiling Point: 169.9°Cat760mmHg
• PKA: 8.23±0.10(Predicted)
• Flash Point: 56.5°C
• PSA: 38.33000
• Density: 1.055g/cm³
• LogP: 0.24020
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

98% ^*data from raw suppliers

D-ProlineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCN1
• Isomeric SMILES: COC(=O)[C@H]1CCCN1
• Uses: D-Proline Methyl Ester, is a building block used for the synthesis of pharmaceutical compounds, such as Eletriptan (E505000) acting as an Antimigrene.

Technology Process of Methyl D-prolinate

There total 30 articles about Methyl D-prolinate 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%

methanol (67-56-1) + rac-Pro-OH (609-36-9,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → methyl pyrrolidine-2-carboxylate (43041-12-9,52183-82-1,2577-48-2)

Guidance literature:

With thionyl chloride; for 16h; Reflux;

Reference yield: 97.0%

2,2,2-trifluoroethylbutyrate (371-27-7) + methyl pyrrolidine-2-carboxylate (43041-12-9,52183-82-1,2577-48-2) → methyl (2R)-pyrrolidine-2-carboxylate (43041-12-9) + (S)-methyl 1-butylpyrrolidine-2-carboxylate

Guidance literature:

With Candida antarctica lipase A on Celite; acetic acid; In various solvent(s); at 25 ℃; for 25h;

DOI:10.1016/j.tet.2003.10.103

Reference yield: 96.0%

N-tritylproline methyl ester (13515-74-7) → methyl pyrrolidine-2-carboxylate (43041-12-9,52183-82-1,2577-48-2)

Guidance literature:

With ammonium cerium (IV) nitrate; water; acetic acid; In dichloromethane; at 20 ℃; for 0.133333h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.10.118

upstream raw materials:

methanol

rac-Pro-OH

N-benzyloxycarbonylproline methyl ester

methyl Pyrrole-2-carboxylate

Downstream raw materials:

N-(tert-butyloxycarbonyl)-L-phenylalanyl-D-proline methyl ester

brevianamide F

N-Benzyloxycarbonyl-(S)-valyl-(S)-leucyl-(R)-proline methyl ester

methyl 1-(2-nitrophenylmethyl)pyrrolidine-2-carboxylate

Refernces

• 1、 -. "Tetrahydropyrido [3, 4-d] pyrimidine derivative and medical application thereof". Paragraph 0351-0359. . Retrieved 2021/03/06.
• 2、 Atobe, Masakazu,Blakemore, David C.,Bond, Paul S.,Chan, Ngai S.,De Fusco, Claudia,Downes, Thomas D.,Firth, James D.,Hubbard, Roderick E.,Jones, S. Paul,Klein, Hanna F.,O'Brien, Peter,Roughley, Stephen D.,Vidler, Lewis R.,Waddelove, Laura,Whatton, Maria Ann,Wheldon, Mary C.,Woolford, Alison J.-A.,Wrigley, Gail L.. "Design and Synthesis of 56 Shape-Diverse 3D Fragments". supporting information. . Retrieved 2020/07/13.