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

Uses

Ethyl 2-(2-oxopyrrolidin-1-yl)acetate is a reagent in the preparation of N-substituted-2-oxopyrrolidinylacetamides which have anticonvulsant activities.

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 
• 64-17-5 ethanol 
• 121562-43-4 trimethylsiloxy(2-oxo-1-pyrrolidinyl)acetic acid ethyl ester 
• 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 
• 62613-80-3 1-ethoxycarbonylmethylpyrrolidine-2,4-dione 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 110104-61-5 ethyl (2,5-dihydro-4-methoxy-2-oxo-1H-pyrrol-1-yl)acetate 

Downstream Products

• 1360827-76-4 C₃₁H₃₂ClF₃N₈O₆S 
• 925-93-9 ethyl [2]alcohol 
• 202197-03-3 1-(3-(4-(1-Benzyl-1H-indazol-5-ylamino)-quinazolin-6-yl)-1,2,4-oxadiazol-5-ylmethyl)-pyrrolidin-2-one 
• 132382-13-9 Trimethyl-{2-[2-(2-oxo-pyrrolidin-1-yl)-acetoxy]-ethyl}-ammonium; iodide 
• 127040-61-3 1-thiocarboxymethylpyrrolidine-2-thione N-(β-phenyl-α-methylethyl)amide 
• 127040-60-2 1-thiocarboxymethylpyrrolidine-2-thione N-(β-phenylethyl) amide 
• 127040-59-9 N-Benzyl-2-(2-thioxo-pyrrolidin-1-yl)-thioacetamide 
• 105479-07-0 1-pyrrolidine-N-(p-chlorobenzylacetamide) 
• 42175-93-9 1-pyrrolidine-N-benzylacetamide 
• 105479-08-1 N-(4-chlorobenzyl)-2-(pyrrolidin-1-yl)ethan-1-amine 
• 105504-31-2 1-(benzylaminoethyl)-2-hydroxypyrrolidine 
• 65875-38-9 N-benzyl-2-(pyrrolidin-1-yl)ethan-1-amine 
• 7482-22-6 N-(cyclohexyl)-2-(2-oxopyrrolidin-1-yl)acetamide 
• 131028-02-9 1-[2-(pyrrolidin-2-one-1-yl) acetyl]-4-(3-chlorophenyl)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.