1-Methyl-5-oxopyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: 1-Methyl-5-oxopyrrolidine-3-carboxylic acid
• CAS No.: 42346-68-9
• Molecular Formula: C6H9NO3
• Molecular Weight: 143.142
• Hs Code.: 2933790090
• European Community (EC) Number: 255-765-5
• DSSTox Substance ID: DTXSID80872025
• Nikkaji Number: J143.882D
• Mol file: 42346-68-9.mol

Synonyms:42346-68-9;1-Methyl-5-oxopyrrolidine-3-carboxylic acid;1-Methyl-2-oxopyrrolidine-4-carboxylic Acid;1-Methyl-5-oxo-pyrrolidine-3-carboxylic acid;1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid;3-Pyrrolidinecarboxylic acid, 1-methyl-5-oxo-;1-Methyl-4-carboxy-2-pyrrolidone;EINECS 255-765-5;MFCD00014102;BRN 0132515;4-22-00-02888 (Beilstein Handbook Reference);1-METHYL-5-OXO-PYRROLIDINE-3-CARBOXYLICACID;C10H10F3NO2;BAS 03107228;1-Methyl-2-oxopyrrolidine-4-carboxylicAcid;EC-000.1926;4-carboxy-1-methylpyrrolidone;SCHEMBL119901;DTXSID80872025;HMS1678N10;BBL009745;STK343943;AKOS000143972;AKOS016040986;AS-5547;SB11648;SB13395;SB13396;AC-23499;N-methyl-2-pyrrolidone-4-carboxylic acid;SY013234;LS-137468;3-Pyrrolidinecarboxylicacid,1-methyl-5-oxo-;BB 0217899;FT-0639786;EN300-33601;1-Methyl-5-oxo-3-pyrrolidinecarboxylic acid #;A872904;Z57472350;F2101-0140

Chemical Property of 1-Methyl-5-oxopyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.26E-06mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 361.7 °C at 760 mmHg
• Flash Point: 172.5 °C
• PSA: 57.61000
• Density: 1.319 g/cm³
• LogP: -0.51280
• Storage Temp.: 2-8°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 178

Purity/Quality:

99.0%Min ^*data from raw suppliers

1-Methyl-5-oxopyrrolidine-3-carboxylic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(CC1=O)C(=O)O
• Uses: 1-Methyl-5-oxopyrrolidine-3-carboxylic Acid is an ondansetron in-adhesive transdermal patch for treating chemotherapy induced nausea and vomiting.

Technology Process of 1-Methyl-5-oxopyrrolidine-3-carboxylic acid

There total 5 articles about 1-Methyl-5-oxopyrrolidine-3-carboxylic acid 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: 91.0%

(±)-methyl 1-methyl-5-oxo-pyrrolidine-3-carboxylate (59857-86-2) → 1-Methyl-5-oxo-3-pyrrolidinecarboxylic Acid (42346-68-9)

Guidance literature:

With sodium hydroxide; In methanol; water; for 24h; Ambient temperature;

DOI:10.1021/jo01293a010

Reference yield: 67.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) + methylamine (74-89-5) → 1-Methyl-5-oxo-3-pyrrolidinecarboxylic Acid (42346-68-9)

Guidance literature:

In water; at 115 ℃; for 1h; under 760.051 Torr; Product distribution / selectivity;

Reference yield:

Dimethyl itakonate (617-52-7) → 1-Methyl-5-oxo-3-pyrrolidinecarboxylic Acid (42346-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / methanol / 1) 1h, 5-10 deg C; 2) 48 h room temp.

2: 91 percent / NaOH / methanol; H₂O / 24 h / Ambient temperature

With sodium hydroxide; In methanol; water;

DOI:10.1021/jo01293a010

upstream raw materials:

2-methylenesuccinic acid

methylamine

(±)-methyl 1-methyl-5-oxo-pyrrolidine-3-carboxylate

Dimethyl itakonate

Downstream raw materials:

N-[3-(4-benzylpiperazin-1-yl)propyl]-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide

N-[3-(4-benzylpiperidin-1-yl)propyl]-1-methyl-N-(3-methylphenyl)-5-oxopyrrolidine-3-carboxamide

N-[3-(4-benzylpiperidin-1-yl)propyl]-1-methyl-N-(2-methylphenyl)-5-oxopyrrolidine-3-carboxamide

Refernces

• 1、 -. "NOVEL COMPOUNDS". Page/Page column 62. . Retrieved 2015/12/17.
• 2、 Imamura, Shinichi,Ishihara, Yuji,Hattori, Taeko,Kurasawa, Osamu,Matsushita, Yoshihiro,Sugihara, Yoshihiro,Kanzaki, Naoyuki,Iizawa, Yuji,Baba, Masanori,Hashiguchi, Shohei. "CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives". . p. 63 - 73. Retrieved 2007/10/03.