34368-52-0

Basic information

• Product Name: (S)-3-HYDROXY-PYRROLIDIN-2-ONE
• Synonyms: (S)-3-Hydroxypyrrolidine-2-one;(S)-3-Hydroxypyrrolidin-2-one;(3S)-3-hydroxypyrrolidin-2-one;(S)-3-Hydroxy-2-pyrrolidone 97%,EE97%;2-Pyrrolidinone, 3-hydroxy-, (3S)-;(S)-3-Hydroxy-ydroxy-pyrrolidin-2-one;(S)-3-Hydroxypyrrolidin-2-one, 95+%;(S)-3-Hydroxy-Pyrrolidin-2-One(WX642165)
• CAS NO: 34368-52-0
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 1308068-626-2
• Mol File: 34368-52-0.mol

Chemical Properties

• Melting Point: 100-102 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• Boiling Point: 363.637 °C at 760 mmHg
• Flash Point: 173.722 °C
• Appearance: /
• Density: 1.292 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• PKA: 12.82±0.20(Predicted)
• CAS DataBase Reference: (S)-3-HYDROXY-PYRROLIDIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-HYDROXY-PYRROLIDIN-2-ONE(34368-52-0)
• EPA Substance Registry System: (S)-3-HYDROXY-PYRROLIDIN-2-ONE(34368-52-0)

Safety Data

• Hazardous Substances Data: 34368-52-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Hydroxy-pyrrolidin-2-one is used as a building block for the synthesis of pharmaceutical compounds. Its chiral nature allows it to be used as a chiral auxiliary in asymmetric catalysis, enabling the production of enantiomerically pure compounds with desired biological activities.
Used in Agricultural Industry:
(S)-3-Hydroxy-pyrrolidin-2-one is used as a precursor in the production of herbicides and fungicides. Its incorporation into these agrochemicals helps in the development of more effective and targeted pest control solutions.
Used in Medicinal Applications:
(S)-3-Hydroxy-pyrrolidin-2-one has shown potential as an anti-inflammatory and anti-tumor agent. Its ability to modulate various biological pathways makes it a promising candidate for the development of new therapeutic agents for the treatment of inflammation and cancer.

InChI:InChI=1/C4H7NO2/c6-3-1-2-5-4(3)7/h3,6H,1-2H2,(H,5,7)/t3-/m0/s1

Upstream product

• 630127-11-6 (S)-4-azido-2-hydroxybutyric acid ethyl ester 
• 194034-43-0 (5S)-5-[2-(benzyloxycarbonylamino)ethyl]-2,2-bis(trifluoromethyl)-1,3-dioxolan-4-one 
• 194034-36-1 ((S)-5-Oxo-2,2-bis-trifluoromethyl-[1,3]dioxolan-4-yl)-acetonitrile 
• 111466-53-6 (S)-3-((trimethylsilyl)oxy)pyrrolidin-2-one 
• 3938-83-8 (S)-4-amino-2-hydroxybutanoic acid 

Downstream Products

• 1228468-93-6 (S)-1-benzyl-3-(benzyloxy)pyrrolidin-2-one 
• 1593701-28-0 (R)-3-[6-(4-fluorophenoxy)pyridin-3-yloxy]pyrrolidin-2-one 
• 1398744-12-1 (3S)-3-hydroxy-1-(3-methylphenyl)pyrrolidin-2-one 
• 1263404-03-0 (R)-(+)-methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((2-oxopyrrolidin-3-yl)oxy)benzoate 
• 77510-50-0 (3R)-3-hydroxy-2-pyrrolidinone 
• 100243-39-8 3-hydroxypyrrolidine 
• 332135-05-4 2-benzyl-3-methoxymethyloxy-6-[(3S)-3-hydroxy-2-pyrrolidinone-1-yl]pyridine 
• 259264-58-9 (S)-(-)-3-[(tert-butyldiphenylsilyl)oxy]pyrrolidin-2-one 
• 259264-78-3 (S)-3-[(tert-butylbis(4-methylphenyl)silyl)oxy]pyrrolidin-2-one 
• 130403-91-7 (3S)-3-[tert-butyl(dimethyl)silyl]oxypyrrolidin-2-one 

Relevant articles and documents

Total Synthesis of Plusbacin A3 and Its Dideoxy Derivative Using a Solvent-Dependent Diastereodivergent Joullié-Ugi Three-Component Reaction

Full details of our synthetic studies toward plusbacin A3 (1), which is a depsipeptide with antibacterial activity, and its dideoxy derivative are described. To establish an efficient synthetic route of 1, a solvent-dependent diastereodivergent Joullié-Ugi three-component reaction (JU-3CR) was used to construct trans-Pro(3-OH) in a small number of steps. Two strategies were investigated toward the total synthesis. In the first synthetic strategy, the key steps were the trans-selective JU-3CR and a macrolactonization at the final stage of the synthesis. The JU-3CR using alkyl isocyanides in 1,1,1,3,3,3-hexafluoroisopropanol provided the trans products, and the coupling of the fragments to prepare the macrocyclization precursor proceeded smoothly. However, attempts toward the macrolactonization did not provide the desired product. Then, the second strategy that included esterification in an initial stage was investigated. Methods for constructing trans-Pro(3-OH) were examined using a convertible isocyanide, which could be converted to a carboxylic acid required for the following amidation. Ester bond formation was achieved through an intermolecular coupling using a hydroxyl-Asp derivative and the corresponding alcohol, and the amidation afforded a linear depsipeptide. The macrolactamization of the linear peptide gave the cyclic depsipeptide, and then the global deprotection accomplished the total synthesis of 1 and its dideoxy derivative.

Revisited Mechanistic Implications of the Joullié-Ugi Three-Component Reaction

The effect of the solvent on the diastereoselectivity of the Joullié-Ugi three-component reaction (JU-3CR) using an α-substituted five-membered cyclic imine is revisited. The cis and trans isomers were generated in toluene and HFIP, respectively. Hammett

STIMULUS-RESPONSIVE POLY(LACTIC-CO-GLYCOLIC)-BASED POLYMERS AND NANOPARTICLES FORMED THEREFROM

PLGA-based polymers include pendant nucleophiles protected with photocleavable protecting groups. Upon deprotection, the polymers degrade rapidly via intramolecular cyclization into small molecules. The polymer may be formulated as a nanoparticle, with an encapsulated payload, which may be an imaging agent, a bioactive agent or a pharmaceutical agent.

INHIBITORS OF HEPATITIS C VIRUS

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SUBSTITUTED BENZAMIDE DERIVATIVES AS GLUCOKINASE (GK) ACTIVATORS

The present invention relates to substituted benzamide derivatives of the general Formula I and their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, diastereomers, prodrugs, metabolites, and polymorphs and can be use

SUBSTITUTED BENZAMIDE DERIVATIVES AS GLUCOKINASE (GK) ACTIVATORS

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Design, synthesis, and cyclization of 4-aminobutyric acid derivatives: Potential candidates as self-immolative spacers

Self-immolative spacers have gained significant interest in recent years due to their utility in numerous prodrug, sensor and drug delivery systems. However, there are a very limited number of spacers that are capable of undergoing spontaneous and rapid reactions under mild conditions. To address this need, 4-aminobutyric acid derivatives were explored as a potential class of self-immolative spacers. Using a modular approach, eleven N- and α-substituted derivatives of 4-aminobutyric acid were synthesized, and their intramolecular cyclizations to γ-lactams were studied. Kinetics experiments were carried out at physiological pH and temperature, and the observed half-lives for the spacers ranged from 2 to 39 s, depending on the molecular structure. In addition, the pH dependence of the cyclization rate was also explored and it was found that cyclization still occurred rapidly at mildly acidic pH. Therefore, this class of compounds exhibits promise for incorporation into a variety of self-immolative systems where rapid cyclization reactions are desired.

Synthetic Method of Optically Pure (S)-3-Hydroxypyrrolidine

A method of preparing optically pure (S)-3-hydroxypyrrolidine is disclosed. The present invention provides a method of economically and industrially preparing optically and chemically pure (S)-3-hydroxypyrrolidine, through a process comprising introducing an amine protecting group by using optically pure 4-amino-(S)-2-hydroxybutylic acid as a starting material, reducing a carboxylic acid group into a primary alcohol, removing the amine protecting group to form an amine salt, halogenating the primary alcohol, and amine cyclization; and through a simple purification process, i.e., distillation under reduced pressure. As another method, the present invention provides a method of preparing optically and chemically pure (S)-3-hydroxypyrrolidine, through a process comprising esterifying optically pure 4-amino-(S)-2-hydroxybutylic acid as a starting material, lactam cyclization, and reduction.

A concise diastereoselective approach to the left-hand side of batzelladine A

A highly diastereoselective three-component coupling reaction has been used in a concise approach to the left-hand side of batzelladine A. The stereoselectivity of this reaction, along with related observations described herein, provides insight into the mechanism of this reaction.

SYNTHETIC METHOD OF OPTICALLY PURE (S)-3-HYDROXYPYRROLIDINE

A method of preparing optically pure (S)-3-hydroxypyrrolidine is disclosed. The present invention provides a method of economically and industrially preparing optically and chemically pure (S)-3-hydroxypyrrolidine, through a process comprising introducing an amine protecting group by using optically pure 4-amino-(S)-2-hydroxybutylic acid as a starting material, reducing a carboxylic acid group into a primary alcohol, removing the amine protecting group to form an amine salt, halogenating the primary alcohol, and amine cyclization; and through a simple purification process, i.e., distillation under reduced pressure. As another method, the present invention provides a method of preparing optically and chemically pure (S)-3-hydroxypyrrolidine, through a process comprising esterifying optically pure 4-amino-(S)-2-hydroxybutylic acid as a starting material, lactam cyclization, and reduction.