Methyl L-prolinate

Base Information

• Chemical Name: Methyl L-prolinate
• CAS No.: 2577-48-2
• Molecular Formula: C6H11 N O2
• Molecular Weight: 129.159
• Hs Code.: 2933990090
• European Community (EC) Number: 219-932-6
• UNII: 0II79F4L0K
• DSSTox Substance ID: DTXSID401311462
• Nikkaji Number: J192.084G
• Wikidata: Q27236825
• Mol file: 2577-48-2.mol

Synonyms:Methyl L-prolinate;2577-48-2;methyl (2S)-pyrrolidine-2-carboxylate;(S)-METHYL PYRROLIDINE-2-CARBOXYLATE;proline, methyl ester;proline methyl ester;L-PROLINE METHYL ESTER;L-Proline, methyl ester;(S)-methylpyrrolidine-2-carboxylate;(S)-proline methyl ester;UNII-0II79F4L0K;(-)-L-Proline methyl ester;0II79F4L0K;EINECS 219-932-6;MFCD03790963;(S)-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER;ProOMe;L-Proline methyl;L-ProOMe;proline-methyl ester;H-Pro-OMe;L-Pro-OMe;NH-Pro-OMe;L-proline-methylester;L-prolin methyl ester;METHYL L-PROLINE;(L)-proline methyl ester;L-Proline Methyl Ester ee;SCHEMBL51793;METHYL (S)-PROLINATE;METHYL PROLINE, (S)-;METHYL PROLINE, (-)-;DTXSID401311462;PROLINE, METHYL ESTER, L-;CAA57748;methyl (2s)-2-pyrrolidinecarboxylate;AKOS000348803;AS-82656;CS-0197089;METHYL (S)-PYRROLIDINE-2-CARBOXYLATE;EN300-69504;(R,S)-Pyrrolidine-2-carboxylic acid methyl ester;(S)-pyrrolidin-2-yl-carboxylic acid methyl ester;A818007;Q27236825

Chemical Property of Methyl L-prolinate

Chemical Property:

• Melting Point: 151-152 °C(Solv: ethyl ether (60-29-7))
• 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:

99% ^*data from raw suppliers

(S)-Methylpyrrolidine-2-carboxylate 95+% ^*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

Technology Process of Methyl L-prolinate

There total 52 articles about Methyl L-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: 100.0%

methanol (67-56-1) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → methyl (2S)-pyrrolidine carboxylate (2577-48-2)

Guidance literature:

With hydrogenchloride; for 2h; Heating;

DOI:10.1016/S0040-4039(00)93484-1

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: 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

L-proline

(S)-N-(tert-butoxycarbonyl)proline methyl ester

(S)-Pyrrolidine-1,2-dicarboxylic acid 1-[2-(4-methoxy-phenyl)-2-oxo-ethyl] ester 2-methyl ester

Downstream raw materials:

(2S)-1-[(2S)-[(benzyloxy)carbonyl]-2-amino-3-(benzylthio)propanoyl]tetrahydro-1H-pyrrole-2-carboxylic acid

1-[N-(α-oxo-isovaleryl)-L-phenylalanyl]-L-proline-methyl ester

1-[N-(2,2-bis-acetylamino-propionyl)-L-phenylalanyl]-L-proline-methyl ester

L-prolinamide

Refernces

• 1、 Varela, Michael C.,Dixon, Seth M.,Price, Michael D.,Merit, Jeffrey E.,Berget, Patrick E.,Shiraki, Saori,Kurth, Mark J.,Schore, Neil E.. "Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts". . p. 3334 - 3339. Retrieved 2007.
• 2、 De La Fuente, M. Carmen,Dominguez, Domingo. "Synthesis of pyrrolo- and pyrido[1,2-a]xanthene [1,9-de]azepines: A study of the azepine ring construction". . p. 8804 - 8810. Retrieved 2007.
• 3、 Prishchenko, Andrey A.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.. "Synthesis of new mono- and bisorganophosphorus proline derivatives with P–C–N moieties". . . Retrieved 2017.
• 4、 Yeh, Ming-Chang P.,Chen, Hsiao-Feng,Huang, Yu-Ya,Weng, Yu-Ting. "Diastereoselective Synthesis of Fluorine-Containing Pyrrolizidines via Triphenylcarbenium Tetrafluoroborate-Promoted Carbofluorination of N-3-Arylpropargylpyrrolidine-Tethered Tertiary Allylic Alcohols". . p. 10892 - 10903. Retrieved 2015.
• 5、 Stoykova, Svetlana A.,Linden, Anthony,Heimgartner, Heinz. "A novel 2 H -azirin-3-amine as a synthon for a sulfur-containing dipeptide segment". . p. 14 - 23. Retrieved 2014.
• 6、 Liljeblad, Arto,Kiviniemi, Anu,Kanerva, Liisa T.. "Aldehyde-based racemization in the dynamic kinetic resolution of N-heterocyclic α-amino esters using Candida antarctica lipase A". . p. 671 - 677. Retrieved 2004.
• 7、 Eschmann, Christian,Song, Lijuan,Schreiner, Peter R.. "London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey–Bakshi–Shibata Reduction". supporting information. p. 4823 - 4832. Retrieved 2021/02/01.
• 8、 -. "Tetrahydropyrido [3, 4-d] pyrimidine derivative and medical application thereof". Paragraph 0273; 0277; 0314-0318. . Retrieved 2021/03/06.