7529-16-0

Basic information

• Product Name: 5-Vinylpyrrolidone
• Synonyms: 5-Vinylpyrrolidon-2;5-VINYLPYRROLIDONE;5-Ethenylpyrrolidin-2-one;5-Ethenyl-2-pyrrolidinone;(±)-5-Vinylpyrrolidin-2-one;5-Vinyl-2-pyrrolidinone;MDL 17637-03;Vigabatrin Related CoMpound A
• CAS NO: 7529-16-0
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• Product Categories: Heterocycles;Impurities
• Mol File: 7529-16-0.mol

Chemical Properties

• Boiling Point: 249.1 °C at 760 mmHg
• Flash Point: 134.7°C
• Appearance: /
• Density: 1.088 g/cm³
• Vapor Pressure: 0.0234mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Chloroform (Sparingly), DMSO, Methanol (Slightly)
• PKA: 15.94±0.40(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 5-Vinylpyrrolidone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Vinylpyrrolidone(7529-16-0)
• EPA Substance Registry System: 5-Vinylpyrrolidone(7529-16-0)

Safety Data

• Hazardous Substances Data: 7529-16-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Vinylpyrrolidone is used as an impurity in the manufacturing of Vigabatrin (V253000), which is a medication used to treat certain seizure disorders. Its presence as an impurity is crucial for the effectiveness and quality control of the final drug product.
Used in Chemical Synthesis:
5-Vinylpyrrolidone is used as a monomer in the synthesis of various polymers and copolymers. Its reactive vinyl group allows it to be polymerized with other monomers, resulting in materials with specific properties tailored for different applications.
Used in Industrial Applications:
5-Vinylpyrrolidone is used as a solvent in the production of certain chemicals and materials. Its solubility properties make it suitable for dissolving a wide range of substances, facilitating various chemical reactions and processes.
Used in Research and Development:
5-Vinylpyrrolidone is utilized in research and development for the exploration of new materials and chemical compounds. Its unique properties and reactivity make it an interesting candidate for studying and developing novel applications in various fields.
Used in USP Related Compound A:
5-Vinylpyrrolidone is also used in the context of the United States Pharmacopeia (USP) as a related compound to Vigabatrin, specifically as USP Related Compound A. This classification is important for the standardization and regulation of the drug's quality and purity.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 847, 1994 DOI: 10.1016/S0040-4039(00)75979-X

InChI:InChI=1/C6H9NO/c1-2-5-3-4-6(8)7-5/h2,5H,1,3-4H2,(H,7,8)

Upstream product

• 60643-86-9 4-amino-5-hexenoic acid 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 1826-67-1 vinyl magnesium bromide 
• 3536-96-7 vinylmagnesium chloride 
• 1577-22-6 5-hexenoic acid 
• 925-90-6 ethylmagnesium bromide 
• 1159991-78-2 N-hydroxyhex-5-enamide 
• 2396-80-7 methyl 5-hexenoate 
• 125348-98-3 2-vinylpyrrolidine hydrochloride 
• 123-56-8 Succinimide 
• 63853-74-7 5-methoxypyrrolidin-2-one 

Downstream Products

• 60643-86-9 4-amino-5-hexenoic acid 
• 1160846-22-9 1-(p-tolylsulfonyl)-5-vinylpyrrolidin-2-one 
• 143418-07-9 (5S)-N-((2R)-2-(3,5-di-t-butyl-4-hydroxyphenyl)thiopropanoyl)-5-ethenylpyrrolidin-2-one 
• 143417-98-5 (5S)-N-((2R)-2-(2,4-di-t-butylphenyloxy)propanoyl)-5-ethenylpyrrolidin-2-one 
• 132114-52-4 (1R,7aR)-1-Acetoxy-2-(diphenyl-phosphinoyloxy)-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-43-3 [2-(1-Acetoxy-allyl)-5-oxo-pyrrolidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester 
• 132114-42-2 [2-(1-Acetoxy-allyl)-5-oxo-pyrrolidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester 
• 132114-34-2 Sodium; (1S,7aR)-1-hydroxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylate 
• 132114-50-2 (1R,7aR)-1-Acetoxy-2-ethylsulfanyl-5-oxo-hexahydro-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-53-5 (1R,7aR)-1-Acetoxy-2-ethylsulfanyl-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-51-3 (1R,7aR)-1-Acetoxy-2,5-dioxo-hexahydro-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-46-6 (1S,7aR)-1-Acetoxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-nitro-benzyl ester 
• 132114-45-5 (1S,7aR)-1-Acetoxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester 
• 132114-47-7 (1S,7aR)-1-Formyloxy-5-oxo-5,6,7,7a-tetrahydro-1H-pyrrolizine-3-carboxylic acid 4-methoxy-benzyl ester 

Relevant articles and documents

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates

x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

A convenient approach for vinylation reaction in the synthesis of 5-vinyl-2-pyrrolidinone, a key intermediate of vigabatrin

A convenient, safe and cost-effective method for carrying out the key vinylation of 5-ethoxy-2-pyrrolidinone (8) in the preparation of 5-vinyl-2-pyrrolidinone (2) in the presence of potassium carbonate is described. This present procedure is developed by replacing inherently hazardous ethyl magnesium bromide with inexpensive and eco-friendly potassium carbonate. The reaction was performed on a multi-gram scale, with vinyl magnesium bromide as the vinylation reagent, in an 81% yield to give the 5-vinyl-2-pyrrolidinone with excellent purity and without the need for chromatography.

A PROCESS FOR THE PREPARATION OF VIGABATRIN

The present invention provides a process for the preparation of vigabatrin of formula (I) comprising of dissolving vigabatrin in water, optionally treating with charcoal, filtering and adding an acid to the reaction mass followed by the addition of an organic solvent and then isolating vigabatrin of formula (I) with high purity.

Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones

We report the Ru-Catalyzed enantioselective annulation of 1,4,2-Dioxazol-5-Ones to furnish ?-Lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-Withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- A nd enantioselectivities; the competing Curtius-Type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the Ca?C and Ca‰iC bonds.

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C - H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C - H bonds was also achieved with remarkable tolerance to the C=C and C=C bonds.

Synthetic method for novel vigabatrin intermediate

The invention relates to a synthetic method for a novel vigabatrin intermediate. According to the invention, through changing of a feeding manner of a reaction, the content of impurities is significantly reduced, and the yield and product purity are improved; meanwhile, through changing of a post-treatment manner, the step of extraction is removed, and the volume of reduced pressure distillation is reduced, so process operations and a solvent amount are significantly reduced, and environmental pollution and cost can be easily reduced. To sum up, compared with the prior art, the synthetic method provided by the invention has the advantages of short period, low cost, simple operation, low environmental pollution, and applicability to industrial production.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.

Synthesis of γ-Lactams by Mild, o-Benzoquinone-Induced Oxidation of Pyrrolidines Containing Oxidation-Sensitive Functional Groups

The late-stage oxidation of substituted pyrrolidines offers good flexibility for the construction of γ-lactam libraries, and especially in recent years the methods for functionalization of pyrrolidine have been available. We reported a new strategy for oxidation of pyrrolidines to γ-lactams: reaction of pyrrolidine with an o-benzoquinone gives an N,O-acetal by direct oxidation of the α-C-H bond of the pyrrolidine ring, and then the N,O-acetal is further oxidized by the o-benzoquinone to the γ-lactam. Because the first oxidation occurs selectively at the α-C-H of the pyrrolidine ring, oxidation-sensitive functional groups (allyl-, vinyl-, hydroxyl-, and amino groups) on pyrrolidine ring are unaffected. The synthetic utility of this novel method was demonstrated by the facile syntheses of (S)-vigabatrin and two analogues.

Process for preparing 4-amino-5-hexenoic acid from succinimide

The present invention relates to a competitive process for the preparation of 4-amino-5-hexenoic acid and intermediates thereof. This compound is a well-known anti-epileptic drug for which several syntheses have been developed, all of them presenting drawbacks. The preparation process according to the present invention is very competitive from an economical point of view and is adapted to industrial scale preparation of 4-amino-5-hexenoic acid.

Cobalt-catalyzed coupling of alkyl iodides with alkenes: Deprotonation of hydridocobalt enables turnover

Completing the cycle: Cobalt complexes I and II were found to catalyze intramolecular alkyl Heck-type coupling reactions of alkyl iodides to alkenes upon irradiation with visible light in the presence of a tertiary amine base. The use of base is key to the catalytic turnover. The compatibility of the method with a broad range of functional groups opens opportunities for synthesis. Copyright