6739-80-6

Basic information

• Product Name: 4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID
• Synonyms: TIMTEC-BB SBB010521;CHEMBRDG-BB 4010425;4-(2-OXOPYRROLIDIN-1-YL)BUTANOIC ACID;4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID;AKOS MSC-0235;4-(2-oxopyrrolidin-1-yl)butanoic acid(SALTDATA: FREE);4-(2-ketopyrrolidin-1-yl)butyric acid;4-(2-oxo-1-pyrrolidinyl)butanoic acid
• CAS NO: 6739-80-6
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19
• Mol File: 6739-80-6.mol

Chemical Properties

• Melting Point: 89.0-89.5 °C
• Boiling Point: 402.6°C at 760 mmHg
• Flash Point: 197.3°C
• Appearance: /
• Density: 1.209g/cm³
• Vapor Pressure: 1.32E-07mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.66±0.10(Predicted)
• CAS DataBase Reference: 4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID(6739-80-6)
• EPA Substance Registry System: 4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID(6739-80-6)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6739-80-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID is used as a key reagent for the preparation of pilsicainide, an antiarrhythmic drug. It is utilized in the synthesis process to create the active pharmaceutical ingredient that helps manage abnormal heart rhythms.
Additionally, 4-(2-OXO-PYRROLIDIN-1-YL)-BUTYRIC ACID is used in the development of oxymethylene analogs, which are sodium channel blockers. These analogs are important in the creation of medications that can treat a variety of conditions by blocking the sodium channels in nerve cells, thereby affecting the transmission of nerve impulses.

InChI:InChI=1/C8H13NO3/c10-7-3-1-5-9(7)6-2-4-8(11)12/h1-6H2,(H,11,12)

Upstream product

• 96-48-0 4-butanolide 
• 590-28-3 potassium cyanate 
• 616-45-5 2-pyrrolidinon 
• 71512-39-5 ethyl 4-(2-oxopyrrolidin-1-yl)butanoate 
• 953088-25-0 diethyl [2-(2-oxopyrrolidin-1-yl)ethyl]malonate 

Downstream Products

• 1372590-92-5 N-(3-{2-[methyl(methylsulfonyl)amino]phenyl}-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-7-yl)-4-(2-oxopyrrolidin-1-yl)butanamide 
• 1372590-77-6 N-(3-{2-[methyl(methylsulfonyl)amino]phenyl}-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-8-yl)-4-(2-oxopyrrolidin-1-yl)butanamide 
• 80662-83-5 1-Benzyloxycarbonyl-5-oxoperhydroazocine 
• 78449-76-0 5-methoxycarbonylmethyl-1-azabicyclo<3.3.0>octane 
• 88069-56-1 ethyl tetrahydro-1H-pyrrolizin-7a(5H)-ylacetate 

Relevant articles and documents

Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins

Intermolecular C-C bond-forming reactions are underdeveloped transformations in the field of biocatalysis. Here we report a photoenzymatic intermolecular hydroalkylation of olefins catalyzed by flavin-dependent 'ene'-reductases. Radical initiation occurs via photoexcitation of a rare high-order enzyme-templated charge-transfer complex that forms between an alkene, α-chloroamide, and flavin hydroquinone. This unique mechanism ensures that radical formation only occurs when both substrates are present within the protein active site. This active site can control the radical terminating hydrogen atom transfer, enabling the synthesis of enantioenriched γ-stereogenic amides. This work highlights the potential for photoenzymatic catalysis to enable new biocatalytic transformations via previously unknown electron transfer mechanisms.

Preparation method of intermediate of synthesis of pilsicainide hydrochloride

The invention provides a preparation method of an intermediate for synthesis of pilsicainide hydrochloride. The method comprises the following steps: step 1, performing a polymerization reaction on butyrolactam (I) and gamma-butyrolactone (II) under strong base and predetermined conditions to form N-(3-carboxypropyl)butyrolactam (III); step 2, performing cyclization on the N-(3-carboxypropyl)butyrolactam(III) at a high temperature in a monoisopropyl malonate solvent, performing condensation on the cyclization product and a monoester malonate to form 7alpha-pyrrolizine-acetate, wherein preferred choice is to produce 7alpha-pyrrolizine-isopropyl acetate (V); and step 3, performing hydrolysis on the 7alpha-pyrrolizine-acetate in an acid to form the corresponding pharmaceutically-acceptable salt. The preparation method provided by the invention avoids expensive or difficult-to-obtain raw materials, avoids use of liquid ammonia in the synthetic process, reduces the reaction steps, and has simple operation, less three waste (waste water, waste gas and solid waste) and a high yield.

Synthesis of an azabicyclic framework towards (±)-actinophyllic acid

Lewis acid mediated intramolecular Mannich reaction between an azocinone and a 3-formylindole was investigated as part of a study towards the synthesis of actinophyllic acid. The intramolecular Mannich reaction resulted in a single diastereomer of the 1-azabicyclo[4.2.1]nonan-5-one core framework, although single crystal X-ray structure analysis revealed that this had the undesired stereochemistry in comparison with the natural product.

Pilsicainide and its oxymethylene analog: Facile alternative syntheses and in vitro testing on human skeletal muscle sodium channels

Facile, alternative synthetic routes gave access to both pilsicainide [N-(2,6-dimethylphenyl)-2-tetrahydro-lH-pyrrolizin-7a(5H)-ylacetamide, 1], a well-known Ic antiarrhythmic drug, and its oxymethylene analog 2. Both compounds were tested on human skeletal muscle voltage-gated sodium channels, hNavl.4, transfected in tsA201 cells. 7a-[2-(2,6-Dimethylphenoxy)ethyl]hexahydro-lH-pyrrolizine (2) behaved as a bioisostere of 1, exerting a 4-fold more potent use-dependent block.

Synthesis of Δ1- and/or Δ8-Dehydroindolizidines and Related Compounds

A facile synthesis of Δ1- and/or Δ8-dehydroindolizidine and related compounds, consisting of dry distillation of γ-(N-2-piperidinonyl)butyric acid over soda-lime, is described.Reductions of these dehydroindolizidines and stereochemistry of 1-methylindolizidine are also described.