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

Base Information

• Chemical Name: (S)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate
• CAS No.: 42435-88-1
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.169
• Hs Code.: 2933790090
• European Community (EC) Number: 838-716-8
• ChEMBL ID: CHEMBL4637402
• DSSTox Substance ID: DTXSID80962475
• Nikkaji Number: J109.250B
• Wikidata: Q27160107
• Mol file: 42435-88-1.mol

Synonyms:42435-88-1;(S)-Methyl 1-methyl-5-oxopyrrolidine-2-carboxylate;L-Proline, 1-methyl-5-oxo-, methyl ester;methyl (2S)-1-methyl-5-oxopyrrolidine-2-carboxylate;PROLINE, 1-METHYL-5-OXO-, METHYL ESTER;methyl 1-methyl-5-oxo-L-prolinate;(S)-Methyl1-methyl-5-oxopyrrolidine-2-carboxylate;SCHEMBL2577902;CHEMBL4637402;CHEBI:88182;methyl 1-methyl-5-oxo-prolinate;DTXSID80962475;N-methyl-5-oxoproline methyl ester;AMY13629;FD7375;MFCD12026427;AKOS016843857;Methyl (2S)-1-methyl-5-oxoprolinate;L-Proline,1-methyl-5-oxo-,methyl ester;AS-49315;(S)-N-methyl-pyroglutamic Acid Methyl Ester;CS-0151231;EN300-132495;Methyl 1-methyl-5-oxo-2-pyrrolidinecarboxylate #;(5)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate;L-Proline, 1-methyl-5-oxo-, methyl ester (9CI);methyl (S)-1-methyl-5-oxopyrrolidine-2-carboxylate;Q27160107

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

Chemical Property:

• Melting Point: 263.7 °C at 760 mmHg
• Boiling Point: 113.3 °C
• PKA: -2.48±0.40(Predicted)
• PSA: 46.61000
• Density: 1.173 g/cm³
• LogP: -0.28190
• Storage Temp.: Sealed in dry,Room Temperature
• 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% ^*data from raw suppliers

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

There total 5 articles about (S)-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: 78.0%

methyl (S)-pyroglutamate (4931-66-2) + methyl iodide (74-88-4) → (S)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate (42435-88-1)

Guidance literature:

In hexane; ethyl acetate; N,N-dimethyl-formamide;

Reference yield: 44.4%

L-Pyroglutamic acid (98-79-3) + methyl iodide (74-88-4) → (S)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate (42435-88-1)

Guidance literature:

L-Pyroglutamic acid; With sodium hydride; In N,N-dimethyl-formamide; for 1h; Cooling with ice; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

Reference yield:

L-Pyroglutamic acid (98-79-3) → (S)-methyl 1-methyl-5-oxopyrrolidine-2-carboxylate (42435-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. H₂SO₄ / benzene / 20 h / Heating

2: 1.) NaH / 1.) benzene, a) room temp., b) 2 h, reflux; 2.) reflux, 24 h

With sodium hydride; sulfuric acid; In benzene;

upstream raw materials:

L-Pyroglutamic acid

methyl iodide

methyl (S)-pyroglutamate

Downstream raw materials:

C₂₄H₂₃ClF₃N₃O₃

1-Methyl-5-hydroxymethyl-pyrrolidinon-(2)

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

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

Refernces

• 1、 -. "Spirocyclic tetrahydroquinazolines". Paragraph 1386; 1389-1391. . Retrieved 2021/07/11.
• 2、 Xing, Hong,Andrud, Kristin W.,Soti, Ferenc,Rouchaud, Anne,Jahn, Stephan C.,Lu, Ziang,Cho, Yeh-Hyon,Habibi, Sophia,Corsino, Patrick,Slavov, Svetoslav,Rocca, James R.,Lindstrom, Jon M.,Lukas, Ron J.,Kem, William R.. "A Methyl Scan of the Pyrrolidinium Ring of Nicotine Reveals Significant Differences in Its Interactions with a7 and a4b2 Nicotinic Acetylcholine Receptors". supporting information. p. 168 - 180. Retrieved 2020/09/12.