35309-35-4

Basic information

• Product Name: METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE
• Synonyms: METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE;5-Oxo-pyrrolidine-3-carboxylic acid methyl ester;3-Pyrrolidinecarboxylic acid, 5-oxo-, Methyl ester;4-(Methoxycarbonyl)-2-oxopyrrolidine;5-ketopyrrolidine-3-carboxylic acid methyl ester;5-oxo-3-pyrrolidinecarboxylic acid methyl ester;5-Oxo-Pyrrolidone-3-carboxylic Acid Methyl ester
• CAS NO: 35309-35-4
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.14
• Mol File: 35309-35-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 62-64 °C
• Boiling Point: 304.717°C at 760 mmHg
• Flash Point: 138.088°C
• Appearance: /
• Density: 1.204
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.465
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• PKA: 15.31±0.40(Predicted)
• CAS DataBase Reference: METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE(35309-35-4)
• EPA Substance Registry System: METHYL 5-OXOPYRROLIDINE-3-CARBOXYLATE(35309-35-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 35309-35-4(Hazardous Substances Data)

Usage

Uses

Methyl 5-Oxopyrrolidine-3-carboxylate has been used as a reactant in the synthesis of tert-butyloxycarbonyl protected 4,5-methano-β-proline.

InChI:InChI=1/C6H9NO3/c1-10-6(9)4-2-5(8)7-3-4/h4H,2-3H2,1H3,(H,7,8)

Upstream product

• 108303-97-5 2-Aminomethyl-succinic acid dimethyl ester; hydrochloride 
• 617-52-7 Dimethyl itakonate 
• 1461706-59-1 C₁₃H₁₅NO₄ 
• 99940-64-4 1-benzyloxy-5-oxo-3-pyrrolidinecarboxylic acid 
• 97-65-4 2-methylenesuccinic acid 
• 7268-43-1 5-oxopyrrolidine-3-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 108303-96-4 2-({[1-Phenyl-meth-(E)-ylidene]-amino}-methyl)-succinic acid dimethyl ester 

Downstream Products

• 83564-49-2 5-thioxopyrrolidine-3-carboxylic acid methyl ester 
• 1610606-91-1 C₁₁H₁₇NO₄ 
• 85310-69-6 pyrrolidin-3-ylmethanol 
• 59379-02-1 tert-butyl 3-formylpyrrolidine-1-carboxylate 
• 114214-69-6 tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 149505-71-5 methyl 1-[(4-methoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylate 
• 1609264-24-5 C₁₃H₁₁FN₂O₃ 
• 1609265-56-6 C₁₃H₁₁FN₂O₃ 
• 1609265-55-5 C₁₃H₁₁FN₂O₃ 
• 1609264-25-6 C₁₂H₉FN₂O₃ 
• 1190896-98-0 N₂-{2-[1,3-dihydro-2H-isoindol-2-yl(methyl)amino]-2-oxoethyl}-N₂-{4-[4-(methoxycarbonyl)-2-oxopyrrolidin-1-yl]-2-methylphenyl}-N₁-{2-[(tert-butoxycarbonyl)(ethyl)amino]ethyl}glycinamide 
• 64320-89-4 4-(hydroxymethyl)-2-pyrrolidinone 
• 85492-64-4 4-[4-((E)-5-Benzyloxy-4,4-dimethyl-3-oxo-pent-1-enyl)-4,5-dihydro-3H-pyrrol-2-ylsulfanyl]-butyric acid ethyl ester 
• 83564-57-2 4-[4-((E)-5-Benzyloxy-3-hydroxy-4,4-dimethyl-pent-1-enyl)-4,5-dihydro-3H-pyrrol-2-ylsulfanyl]-butyric acid ethyl ester 

Relevant articles and documents

First total synthesis of (±)-3-hydroxy-11-norcytisine: Structure confirmation and biological characterization

(Chemical Equation Presented) The first total synthesis of the natural product 3-hydroxy-11-norcytisine (1), structurally related to cytisine (2), a benchmark ligand at neuronal nicotlnic acetylcholine receptors (NNRs), has been achieved. The synthesis permits the unambiguous confirmation of the structure originally proposed for 1 and has enabled initial biological characterization of 1 and its related compounds against NNRs.

Synthesis of Boc-protected 4,5-methano-β-proline

An efficient method for the preparation of Boc-protected 4,5-methano-β-proline - a novel bicyclic cyclopropane-containing β-amino acid - was developed, starting from readily available itaconic acid. A modified Simmons-Smith reaction was used for the construction of the cyclopropane ring. The method allowed for the synthesis of both cis and trans isomers of the title compound in 49% total yield and can be employed for gram-scale preparations. An approach to the preparation of methyl 5-oxopyrrolidine-3-carboxylate, which is one of the key intermediates in the synthetic scheme, on a multigram scale was also developed.

THERAPEUTIC AGENT FOR DIABETES

A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.