molecular formula C8H13NO4 B144351 Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate CAS No. 62613-81-4

Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate

Cat. No.: B144351
CAS No.: 62613-81-4
M. Wt: 187.19 g/mol
InChI Key: YDBONCLBTWFUPF-UHFFFAOYSA-N
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Description

Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate is a chemical compound with the molecular formula C8H13NO4. It is a derivative of pyrrolidine, a five-membered nitrogen-containing heterocycle.

Preparation Methods

Synthetic Routes and Reaction Conditions

Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate can be synthesized through the esterification of 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetic acid with ethanol in the presence of an acid catalyst. The reaction typically involves refluxing the reactants to achieve the desired product .

Industrial Production Methods

In an industrial setting, the synthesis of this compound may involve continuous flow reactors to optimize reaction conditions and improve yield. The use of catalysts and solvents that are easily recoverable and recyclable is also common to enhance the sustainability of the process .

Chemical Reactions Analysis

Types of Reactions

Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate undergoes various chemical reactions, including:

Common Reagents and Conditions

Major Products Formed

Scientific Research Applications

Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate has several applications in scientific research:

    Chemistry: Used as an intermediate in the synthesis of more complex organic molecules.

    Biology: Studied for its potential biological activity and interactions with enzymes.

    Medicine: Investigated for its potential therapeutic effects, particularly in the development of new drugs.

    Industry: Utilized in the production of specialty chemicals and materials.

Mechanism of Action

The mechanism of action of Ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate involves its interaction with specific molecular targets, such as enzymes or receptors. The compound may act as an inhibitor or activator, depending on the context of its use. The pathways involved often include modulation of enzyme activity or alteration of receptor binding .

Comparison with Similar Compounds

Similar Compounds

Uniqueness

This compound is unique due to the presence of both an ester and a hydroxyl group, which allows it to participate in a wider range of chemical reactions compared to its analogs. This dual functionality makes it a versatile intermediate in organic synthesis and a valuable compound in medicinal chemistry .

Properties

IUPAC Name

ethyl 2-(4-hydroxy-2-oxopyrrolidin-1-yl)acetate
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI

InChI=1S/C8H13NO4/c1-2-13-8(12)5-9-4-6(10)3-7(9)11/h6,10H,2-5H2,1H3
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

YDBONCLBTWFUPF-UHFFFAOYSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CCOC(=O)CN1CC(CC1=O)O
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C8H13NO4
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

DSSTOX Substance ID

DTXSID10978180
Record name Ethyl (4-hydroxy-2-oxopyrrolidin-1-yl)acetate
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Molecular Weight

187.19 g/mol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

CAS No.

62613-81-4
Record name 1-Pyrrolidineacetic acid, 4-hydroxy-2-oxo-, ethyl ester
Source CAS Common Chemistry
URL https://commonchemistry.cas.org/detail?cas_rn=62613-81-4
Description CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
Record name Ethyl 4-hydroxy-2-oxopyrrolidine-1-acetate
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Record name Ethyl (4-hydroxy-2-oxopyrrolidin-1-yl)acetate
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Record name Ethyl 4-hydroxy-2-oxopyrrolidine-1-acetate
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Synthesis routes and methods I

Procedure details

To a solution of 51.5 g. 4-trimethylsilyloxypyrrolidin-2-one in 500 ml. anhydrous acetonitrile are added 133 ml. ethyl bromoacetate. The solution is heated to 50° C. and 26.7 g. of 80% sodium hydride (dispersion in mineral oil) are slowly added in small amounts. When the addition is completed, the reaction mixture is heated under reflux for 30 minutes and then cooled to ambient temperature. To the reaction mixture obtained containing ethyl 2-(4-trimethylsilyloxypyrrolidin-2-on-1-yl)-acetate (b.p. 160° C./3 mm.Hg) are added 50 ml. 1 N hydrochloric acid. The reaction mixture is stirred for 30 minutes and then evaporated to dryness. The residue obtained is chromatographed on a silica gel column, using ethyl acetate as the elution agent, 45 g. ethyl 2-(4-hydroxypyrrolidin-2-on-1-yl)-acetate being obtained; b.p. 180° C./0.8 mm.Hg; Rf 0.17 (silica gel; eluant ethyl acetate).
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Synthesis routes and methods II

Procedure details

A solution of 0.16 g ethyl 2-oxo-4-(tetrahydropyran-2-yl)-1-pyrrolidineacetate is dissolved in 5 ml ethanol containing 16 mg pyridinium p-toluenesulphonate. The mixture is heated 4 h at 35° , the ethanol is evaporated and the residue chromatographed on silica. The title compound is obtained as a colourless oil in 62% yield.
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ethyl 2-oxo-4-(tetrahydropyran-2-yl)-1-pyrrolidineacetate
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62%

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