(R)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate

Base Information

• Chemical Name: (R)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate
• CAS No.: 122742-14-7
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.169
• DSSTox Substance ID: DTXSID60494067
• Nikkaji Number: J2.907.183G
• Wikidata: Q72494306
• Mol file: 122742-14-7.mol

Synonyms:122742-14-7;(R)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate;methyl (2R)-1-methyl-5-oxopyrrolidine-2-carboxylate;1-Methyl-5-oxo-D-proline methyl ester;METHYL (R)-1-METHYL-5-OXOPYRROLIDINE-2-CARBOXYLATE;D-Proline, 1-methyl-5-oxo-, methyl ester;Methyl 1-methyl-5-oxo-D-prolinate;SCHEMBL1587388;DTXSID60494067;ABAOXDQXQHQRFA-RXMQYKEDSA-N;AMY13598;AKOS006319193;BS-19509;EN300-374715

Chemical Property of (R)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.0101mmHg at 25°C
• Refractive Index: 1.476
• Boiling Point: 263.7 °C at 760 mmHg
• PKA: -2.48±0.40(Predicted)
• Flash Point: 113.3 °C
• PSA: 46.61000
• Density: 1.173 g/cm³
• LogP: -0.28190
• Storage Temp.: 2-8°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 157.07389321
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-Methyl1-methyl-5-oxopyrrolidine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(CCC1=O)C(=O)OC
• Isomeric SMILES: CN1[C@H](CCC1=O)C(=O)OC

Technology Process of (R)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate

There total 4 articles about (R)-Methyl 1-methyl-5-oxopyrrolidine-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: 84.0%

methyl (2R)-pyroglutamate (64700-65-8) + methyl iodide (74-88-4) → (R)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate (122742-14-7)

Guidance literature:

With potassium carbonate; In acetonitrile; at 0 - 80 ℃; for 72h;

Reference yield:

methyl (2R)-pyroglutamate (64700-65-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (R)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate (122742-14-7)

Guidance literature:

With sodium hydride; at 0 ℃; for 2h;

Reference yield:

D-pyrrolidone-5-carboxylic acid (4042-36-8) → (R)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate (122742-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 6 h / -20 °C

2: 1.) Na / 1.) toluene, -20 deg C, 2.) toluene, DMF, RT, overnight

With thionyl chloride; sodium;

DOI:10.1016/0040-4020(96)00743-0

upstream raw materials:

D-pyrrolidone-5-carboxylic acid

methyl iodide

methyl (2R)-pyroglutamate

N,N-dimethyl-formamide

Downstream raw materials:

N-methyl D-5-Oxoproline methyl amide

(5R)-5-(aminomethyl)-1-methyl-pyrrolidin-2-one

2(S)-<(tert-butyloxycarbonyl)amino>-3-cyclohexyl-1(S)-hydroxy-1-(1-methyl-5(R)-ethenyl-2-oxopyrrolidin-3(S)-yl)propane

1-methyl-5(R)-vinyl-2-pyrrolidinone

Refernces

• 1、 -. "NOVEL INDOLE DERIVATIVES AND THEIR USE IN NEURODEGENERATIVE DISEASES". Paragraph 0836-0837. . Retrieved 2016/11/24.
• 2、 Williamson, David A.,Bowler, Bruce E.. "Synthesis of a beta-turn forming depsipeptide for hydrogen bond mediated electron transfer studies". . p. 12357 - 12372. Retrieved 2007/10/03.