52450-32-5

Basic information

• Product Name: ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE
• Synonyms: ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE;ETHYL 4-PHENYL-2-PYRROLIDONE-3-CARBOXYLATE;4-PHENYL-2-PYRROLIDONE-3-CARBOXYLIC ACID ETHYL ESTER;3-CARBETHOXY-4-PHENYLPYRROLIDINONE;4-PHENYL-3-CARBETHOXY-PYRROLIDONE-2;4-Phenyl-3-carbethoxy-2-pyrrolidone;Ethyl 2-oxo-4-phenylpyrrolidine-3-carboxylate;2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine
• CAS NO: 52450-32-5
• Molecular Formula: C₁₃H₁₅NO₃
• Molecular Weight: 233.26
• Product Categories: Aromatic Esters;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines
• Mol File: 52450-32-5.mol

Chemical Properties

• Boiling Point: 418.3 °C at 760 mmHg
• Flash Point: 206.8 °C
• Appearance: /
• Density: 1.168 g/cm³
• Vapor Pressure: 3.3E-07mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE(52450-32-5)
• EPA Substance Registry System: ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE(52450-32-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 52450-32-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE is used as an intermediate in the synthesis of various pharmaceutical compounds for its unique molecular structure and properties. It plays a crucial role in the development of new drugs and medicinal compounds, contributing to the advancement of healthcare and medicine.
Used in Research and Development:
ETHYL 2-OXO-4-PHENYL-3-PYRROLIDINECARBOXYLATE is used as a research chemical for studying its properties, reactions, and potential applications in the field of chemistry and pharmaceuticals. It aids scientists and researchers in understanding its behavior and exploring its potential uses in creating innovative and effective drugs and treatments.

InChI:InChI=1/C13H15NO3/c1-2-17-13(16)11-10(8-14-12(11)15)9-6-4-3-5-7-9/h3-7,10-11H,2,8H2,1H3,(H,14,15)

Synthetic route

diethyl 2-(3-nitrophenylethyl)malonate (71639-13-9) → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
With ammonium chloride; zinc In water at 60 - 65℃;	80%
With hydrogen; palladium on activated charcoal In ethanol at 60℃; under 6840 - 7600 Torr; for 2.4h;	3.66 g

(+-)-<2-nitro-1-phenyl-ethyl>-malonic acid diethyl ester → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
With hydrogenchloride; nickel Hydrogenation;
With ethanol; nickel Hydrogenation;

(+-)--malonic acid diethyl ester → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
With ethanol; nickel at 100℃; under 73550.8 Torr; Hydrogenation;
With methanol; nickel at 20℃; under 2206.5 Torr; Hydrogenation;

2-oxo-4-phenylpyrrolidine-3-carboxylic acid (77519-55-2) → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
sulfuric acid In ethanol at 120℃; for 0.166667h;

diethyl malonate (105-53-3) → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4 h / -20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 20 - 30 °C View Scheme

2-nitroacetophenone (614-21-1) → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 4 h / -20 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 20 - 30 °C View Scheme

C15H17NO6 → 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20 - 30℃; Solvent;

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) + ethyl iodide (75-03-6) → 3-ethyl-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid ethyl ester (861035-62-3)

Conditions	Yield
With sodium ethanolate

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) + methyl iodide (74-88-4) → 3-methyl-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid (105909-99-7)

Conditions	Yield
With sodium methylate Erwaermen des Reaktionsprodukts mit methanol. KOH;

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 4-phenylpyrrolidin-2-one (1198-97-6)

Conditions	Yield
With hydrogenchloride; ethanol; water
Multi-step reaction with 2 steps 1: ethanolic KOH 2: 175 °C View Scheme
With sodium carbonate for 6h; Reagent/catalyst; Reflux;	3.3 g

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 2-oxo-4-phenylpyrrolidine-3-carboxylic acid (77519-55-2)

Conditions	Yield
With potassium hydroxide
Stage #1: 2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine With water; sodium hydroxide In methanol at 20℃; for 13h; Stage #2: With hydrogenchloride In methanol; water

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 4-amino-3-phenylbutanoic acid (1078-21-3)

Conditions	Yield
With hydrogenchloride

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 3-ethyl-4-phenyl-pyrrolidine

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanolic sodium ethylate 2: methanol. KOH 3: unter vermindertem Druck 4: butyl alcohol; sodium View Scheme

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 3-ethyl-4-phenyl-pyrrolidin-2-one (858274-65-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanolic sodium ethylate 2: methanol. KOH 3: unter vermindertem Druck View Scheme

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 3-ethyl-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid (861035-64-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanolic sodium ethylate 2: methanol. KOH View Scheme

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 2-oxo-4-phenyl-3-pyrrolidinecarboxylic acid N'-[1-(3-bromo-phenyl)-ethyl]-hydrazide

Conditions	Yield
With sodium cyanoborohydride In ethanol; acetic acid at 20℃; for 2h;

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine (52450-32-5) → 2-oxo-4-phenylpyrrolidine-3-carbocylic acid hydrazide (331417-35-7)

Conditions	Yield
With hydrazine In ethanol at 120℃; for 0.333333h;

Upstream product

• 71639-13-9 diethyl 2-(3-nitrophenylethyl)malonate 
• 77519-55-2 2-oxo-4-phenylpyrrolidine-3-carboxylic acid 
• 105-53-3 diethyl malonate 
• 614-21-1 2-nitroacetophenone 
• 185067-05-4 ethyl 2-carbethoxy-3-cyano-3-phenylpropionate 
• 5292-53-5 diethyl benzalmalonate 

Downstream Products

• 861035-62-3 3-ethyl-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid ethyl ester 
• 105909-99-7 3-methyl-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid 
• 1198-97-6 4-phenylpyrrolidin-2-one 
• 77519-55-2 2-oxo-4-phenylpyrrolidine-3-carboxylic acid 
• 1078-21-3 4-amino-3-phenylbutanoic acid 
• 331417-35-7 2-oxo-4-phenylpyrrolidine-3-carbocylic acid hydrazide 
• 67159-52-8 (3R*,4S*)-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid 
• 61586-46-7 (-)-(R)-3-Phenylpyrrolidine 
• 62624-46-8 (S)-(+)-3-phenylpyrrolidine 
• 71657-88-0 (4R)-4-phenyl-2-pyrrolidone 
• 62624-45-7 (S)-4-phenyl-1-tosylpyrrolidin-2-one 
• 128372-78-1 (-)-(S)-1-tert-Butoxycarbonyl-4-phenyl-2-pyrrolidinone 
• 128372-78-1 (+)-(R)-1-tert-Butoxycarbonyl-4-phenyl-2-pyrrolidinone 
• 138812-85-8 (3S,4S)-N-<(1R)-2-Hydroxy-1-phenylethyl>-2-oxo-4-phenylpyrrolidine-3-carboxamide 

Relevant articles and documents

Synthesis method of 4-phenyl-2-pyrrolidone

The invention discloses a synthesis method of 4-phenyl-2-pyrrolidone, which comprises the following steps: by using diethyl malonate and 2-nitro-1-phenethyl ketone as raw materials, carrying out condensation reaction by using a strong Lewis base to obtain an intermediate 1, and reacting the intermediate 1 in an organic solvent under the action of palladium-carbon catalytic hydrogenation to obtain an intermediate 3-(3-methoxy carboxyl -4-phenyl-2-pyrrolidone); and finally, carrying out decarboxylation reaction under the alkaline condition of an organic solvent to obtain the final 4-phenyl-2-pyrrolidone. In addition, 4-phenyl-2-pyrrolidone can also be prepared through a Fork alkylation reaction of pyrrolidone and halogenated benzene by a one-step method. The method disclosed by the invention has the characteristics of readily available raw materials, simple reaction conditions, high yield and the like.

Asymmetric cyanation of activated olefins with ethyl cyanoformate catalyzed by a modular titanium catalyst

"Chemical Equation Presented" Asymmetric cyanation of a class of easily available olefins with a favorable cyanide source ethyl cyanoformate (CNCOOEt) was realized by an interesting modular catalyst. High yields and ee values were obtained for a range of substrates under solvent-free and mild reaction conditions. The products obtained could be easily transformed to the enantioenriched useful intermediates 5,6, and pharmaceutically Important γ-aminobutyric acid 7.

Tandem reductive cyclisation of diethyl 2-(2-nitro-1-arylethyl)malonate by zinc and ammonium chloride in aqueous medium

A tandem reductive cyclisation of diethyl 2-(2-nitro-1-arylethyl)malonate by zinc and ammonium chloride in aqueous medium leading to a one pot synthesis of ethyl 2-oxo-4-arylpyrrolidine-3-carboxylate in good yield has been described.

PAR2-MODULATING COMPOUNDS AND THEIR USE

This invention relates to compounds, their uses for the elucidation of PAR2 activity and their uses for the treatment or prevention of diseases or disorders related to PAR2 activity, wherein the compound has the general chemical structure: (I).

Resolution of 4-phenyl-2-pyrrolidinone: A versatile synthetic intermediate

A resolution of 4-phenyl-2-pyrrolidinone is described. The resulting enantiomerically pure pyrrolidinones are exploited as precursor to 3-phenylpyrrolidines and 3-phenyl-γ-amino acids (4-amino-3-phenylbutanoic acid derivatives).