61516-73-2

Basic information

• Product Name: ethyl 2-oxopyrrolidine-1-acetate
• Synonyms: ethyl 2-oxopyrrolidine-1-acetate;ETHYL 2-OXOPYRROLIDIN-2-YLACETATE;2-Pyrrolidone-N-acetic acid ethyl ester;Einecs 262-828-0;1-Pyrrolidineacetic acid, 2-oxo-, ethyl ester;2-(oxo-pyrrolidin-1-yl)-acetic acid ethyl ester;1-(Ethoxycarbonylmethyl)-2-pyrrolidone;Ethyl (2-oxo-1-pyrrolidinyl)acetate
• CAS NO: 61516-73-2
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19372
• EINECS: 262-828-0
• Mol File: 61516-73-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 155-158℃
• Boiling Point: 303.6 °C at 760 mmHg
• Flash Point: 137.4 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4670 (20℃)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -0.79±0.20(Predicted)
• CAS DataBase Reference: ethyl 2-oxopyrrolidine-1-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-oxopyrrolidine-1-acetate(61516-73-2)
• EPA Substance Registry System: ethyl 2-oxopyrrolidine-1-acetate(61516-73-2)

Safety Data

• Hazardous Substances Data: 61516-73-2(Hazardous Substances Data)

Usage

Description

Ethyl 2-oxopyrrolidine-1-acetate, also known as Ethyl 2-(2-oxopyrrolidin-1-yl)acetate, is an organic compound that serves as a reagent in the synthesis of various pharmaceutical compounds. It is characterized by its unique structure, which includes a pyrrolidine ring and an ester group, making it a versatile building block in organic chemistry.

Uses

Used in Pharmaceutical Industry:
Ethyl 2-oxopyrrolidine-1-acetate is used as a reagent for the preparation of N-substituted-2-oxopyrrolidinylacetamides, which possess anticonvulsant activities. These compounds are of interest in the development of new medications for the treatment of epilepsy and other seizure disorders due to their potential to modulate neuronal excitability and reduce seizure frequency.

InChI:InChI=1/C8H13NO3/c1-2-6(8(11)12)9-5-3-4-7(9)10/h6H,2-5H2,1H3,(H,11,12)

Upstream product

• 616-45-5 2-pyrrolidinon 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 62613-80-3 1-ethoxycarbonylmethylpyrrolidine-2,4-dione 
• 121562-43-4 trimethylsiloxy(2-oxo-1-pyrrolidinyl)acetic acid ethyl ester 
• 64-17-5 ethanol 
• 139885-33-9 1-(1-bromo-1-ethoxycarbonylmethyl)-2-pyrrolidone 
• 139885-17-9 1-(1-hydroxy-1-ethoxycarbonylmethyl)-2-pyrrolidone 
• 142274-10-0 ethyl (4-acetoxy-1,5-dihydro-2-oxo-2H-pyrrol-1-yl)acetate 
• 121562-44-5 1--2-pyrrolidinone 
• 110104-61-5 ethyl (2,5-dihydro-4-methoxy-2-oxo-1H-pyrrol-1-yl)acetate 

Downstream Products

• 53934-76-2 N-(2-pyrrolidone)-2-acetic acid 
• 131028-06-3 1-(2-ethoxyethyl)-4-ethylpiperazine 
• 131027-91-3 YKAe1003 
• 131027-98-0 1-[2-Oxo-2-(4-p-tolyl-piperazin-1-yl)-ethyl]-pyrrolidin-2-one 
• 131027-97-9 1-[2-Oxo-2-(4-m-tolyl-piperazin-1-yl)-ethyl]-pyrrolidin-2-one 
• 113933-07-6 1-[2-(2-oxopyrrolidin-1-yl)-acetyl]-4-benzylpiperazine 
• 131027-96-8 1-[2-Oxo-2-(4-o-tolyl-piperazin-1-yl)-ethyl]-pyrrolidin-2-one 
• 131027-93-5 1-{2-Oxo-2-[4-(2-phenoxy-ethyl)-piperazin-1-yl]-ethyl}-pyrrolidin-2-one 
• 68497-62-1 pramiracetam 
• 127040-58-8 1-carboxymethylpyrrolidone-2 N-(2-adamantyl)amide 
• 110231-11-3 1-<2-(4-difenilmetil-piperazin-1-il)-2-oxo-etil>pirrolidin-2-one 
• 131028-01-8 1-{2-Oxo-2-[4-(2,4,6-trimethyl-phenyl)-piperazin-1-yl]-ethyl}-pyrrolidin-2-one 
• 131027-94-6 1-{2-Oxo-2-[4-(2-phenylsulfanyl-ethyl)-piperazin-1-yl]-ethyl}-pyrrolidin-2-one 
• 131027-92-4 1-(2-methylthioethyl)-4-((2-oxo-1-pyrrolidinyl)acetyl)piperazine 

Relevant articles and documents

Silica gel and microwave-promoted synthesis of dihydropyrrolizines and tetrahydroindolizines from enaminones

A wide range of N-(ethoxycarbonylmethyl)enaminones, prepared by the Eschenmoser sulfide contraction between N-(ethoxycarbonylmethyl) pyrrolidine-2-thione and various bromomethyl aryl and heteroaryl ketones, underwent cyclization in the presence of silica gel to give ethyl 6-(hetero)aryl-2,3-dihydro-1H-pyrrolizine-5-carboxylates within minutes upon microwave heating in xylene at 150 °C. Instead of functioning as a nucleophile, the enaminone acted as an electrophile at its carbonyl group during the cyclization. Yields of the bicyclic products were generally above 75%. The analogous microwave-assisted reaction to produce ethyl 2-aryl- 5,6,7,8-tetrahydroindolizine-3-carboxylates from (E)-ethyl 2-[2-(2-oxo-2-arylethylidene)piperidin-1-yl]acetates failed in nonpolar solvents, but occurred in ethanol at lower temperature and microwave power, although requiring much longer time. A possible mechanism for the cyclization is presented, and further functionalization of the newly created pyrrole ring in the dihydropyrrolizine core is described.

Ugi Four-Center Three-Component Reaction as a Direct Approach to Racetams

We report the synthesis of racetams, a diverse class of small molecule drugs, by means of the Ugi four-center three-component reaction (U4C-3CR). For the first time, γ-aminobutyric acid is employed as bifunctional input in the Ugi reaction. This protocol is simple, general, and allows one-pot access to a range of drugs and bioactive small molecules.

Structure dependence in the solvolysis kinetics of amino acid esters

To better understand acyl transfer reactions of oligopeptides, seventeen N-acyl amino acid esters were solvolyzed in mildly basic methanol-d4. All show pseudo-first-order kinetics by 1H NMR. The rate constant varies up to 400-fold with the identity of the amino acid and up to 6200-fold with the identity of the N-acyl group. The impact of the N-acyl group on the rate constant is discussed in terms of crowding, amide conformation, and amide C{double bond, long}O bond character.