110958-23-1

Basic information

• Product Name: (S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one
• Synonyms: (S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one
• CAS NO: 110958-23-1
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196
• EINECS: -0
• Mol File: 110958-23-1.mol

Chemical Properties

• Boiling Point: 456.8±38.0 °C(Predicted)
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• PKA: 15.45±0.40(Predicted)
• CAS DataBase Reference: (S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one(110958-23-1)
• EPA Substance Registry System: (S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one(110958-23-1)

Safety Data

• Hazardous Substances Data: 110958-23-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one is used as a key compound in the development and synthesis of new drugs for various medical applications. Its unique structure and properties contribute to the creation of innovative pharmaceuticals that can address a range of health issues.
Used in Organic Synthesis:
In the field of organic chemistry, (S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one serves as a building block for the production of various compounds. Its versatility allows it to be incorporated into different chemical reactions, leading to the synthesis of a wide array of molecules with diverse applications.
Used in Chemical Production:
(S)-5-(piperidine-1-carbonyl)pyrrolidin-2-one is also utilized as an essential component in the manufacturing process of certain chemical products. Its presence in these processes can enhance the properties of the final products, making them more effective or efficient for their intended uses.

Upstream product

• 6091-44-7 piperidine hydrochloride 
• 4931-66-2 methyl (S)-pyroglutamate 
• 110-89-4 piperidine 
• 98-79-3 L-Pyroglutamic acid 
• 511543-55-8 (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octane-4,8-dione 

Downstream Products

• 65921-41-7 (S)-2-(1-piperidinylmethyl)pyrrolidine 

Relevant articles and documents

DIBAL-H-H2NR and DIBAL-H-HNR1R2·HCl complexes for efficient conversion of lactones and esters to amides

The reaction of a lactone or an ester with organoaluminum species generated from DIBAL-H-H2NR or DIBAL-H-HNR1R2·HCl complexes provided efficient methods for preparation of amides. Conditions were defined for the preparation of both secondary and tertiary amides, including Weinreb amides in excellent yields.

Insights into the reaction mechanism of the prolyl - Acyl carrier protein oxidase involved in anatoxin-a and homoanatoxin-a biosynthesis

Anatoxin-a and homoanatoxin-a are two potent cyanobacterial neurotoxins. We recently reported the identification of the gene cluster responsible for the biosynthesis of these toxins as well as the in-vitro reconstitution of the first steps of this biosynthesis. We now report experimental evidence supporting the proposed reaction mechanism of AnaB, a flavoprotein homologous to acyl-CoA dehydrogenase. AnaB catalyzes the two-electron oxidation of prolyl-AnaD, which is proline linked to the acyl carrier protein holo-AnaD, to dehydroprolyl-AnaD using oxygen as the second substrate. AnaB is thus an oxidase. By using liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS), we have identified and characterized dehydroprolyl-AnaD, the AnaB product. We estimated an apparent catalytic constant of 1 min- 1 for AnaB catalysis. We synthesized several deuterium-labeled prolines and enzymatically transformed them into their corresponding prolyl-AnaD. These deuterium-labeled prolyl-AnaDs were oxidized in the presence of AnaB, and the deuterium labeling in the remaining substrate and in the product was determined by LC-MS/MS. The data supported a reaction mechanism starting with a rapid enolization followed by a slow oxidation to give the conjugated imine, which in turn was isomerized to pyrroline-5-carboxyl-AnaD. We also showed that cis- and trans-4-fluoro-l-prolyl- AnaD and 3,4-dehydro-l-prolyl-AnaD were transformed into pyrrole-2-carboxyl-AnaD by AnaB. Thus, the 4-fluoro-analogues experienced a β-elimination supporting the AnaB-catalyzed aza - allylic isomerization. We identified by sequence alignment the AnaB active site base, Glu244. We produced, purified, and characterized the E244A AnaB mutant, which is inactive, supporting the catalytic role of E244 as a base.

Synthesis of chiral diamines using novel 2-trichloromethyloxazolidin-4-one precursors derived from 5-oxo-proline and proline

Efficient syntheses of chiral vicinal diamines derived from (S)-oxo-proline and (S)-proline are described. The novel diastereomerically pure precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo-[3.3.0]-octan-4,8-dione 3 and its enantiomer are readily available by reaction of the inexpensive enantiomers of 5-oxo-proline with chloral. Compound 3 reacts with primary and secondary amines to afford the 5-oxo-prolylamides 4 in quantitative yield. In contrast, the (S)-proline-derived precursor (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 6 gave (S)-N-formylprolylamides 9 and/or (S)-prolylamides 8 depending on the reaction conditions. Upon reduction with LiAlH4, amides 4 and 9 afforded the proline-derived (S)-2-(alkylaminomethyl)pyrrolidines 1 and (S)-N-methyl-2-(alkylaminomethyl)-pyrrolidines 5 in 70-90% yields.