Pyrrolidine-2,3-dione

Base Information

• Chemical Name: Pyrrolidine-2,3-dione
• CAS No.: 36069-76-8
• Molecular Formula: C4H5NO2
• Molecular Weight: 99.09
• Hs Code.: 2933990090
• Mol file: 36069-76-8.mol

Synonyms:3-N-tert-butoxycarbonyl-aminomethylpyrrolidine;pyrrolidindione;tert-butyl pyrrolidin-3-ylmethylcarbamate;pyrrolidinedione;3-N-Boc-Aminomethyl pyrrolidine;pyrrolidine-2,3-dione;azolidinedione;pyrrolidindion;2,3-Pyrrolidin-dion;dioxo-pyrrolidine;

Chemical Property of Pyrrolidine-2,3-dione

Chemical Property:

• PSA: 46.17000
• LogP: -0.59580
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Pyrrolidine-2,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Pyrrolidine-2,3-dione is a heterocyclic diketone structure that serves as a key pharmacophore in bioactive compounds such as leopolic acid A, demonstrating antimicrobial properties. Its synthesis involves strategic steps like Dieckmann cyclization to form the core ring, though intermediates with this moiety can be unstable. The scaffold's presence in antimicrobial agents highlights its potential for developing novel antibiotics, particularly amid rising resistance concerns. Further exploration of pyrrolidine-2,3-dione derivatives could optimize their biological activity and therapeutic applications.

Technology Process of Pyrrolidine-2,3-dione

There total 3 articles about Pyrrolidine-2,3-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-hydroxy-2-pyrrolidinone (15166-68-4,78340-48-4) → 2,3-Pyrrolidin-dion (36069-76-8)

Guidance literature:

With chromic acid; In acetone; at 20 - 25 ℃; for 0.25h;

Reference yield:

3,3-Dimethoxypyrrolidin-2-one (106180-87-4) → 2,3-Pyrrolidin-dion (36069-76-8)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 0.5h; Ambient temperature;

Reference yield:

→ 2,3-Pyrrolidin-dion (36069-76-8)

Guidance literature:

Verb.7: 1) Hydrolyse 2) Decarboxylierung;

upstream raw materials:

3-hydroxy-2-pyrrolidinone

3,3-Dimethoxypyrrolidin-2-one

Refernces

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

10.3762/bjoc.12.159

The research focuses on the first total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity derived from a fungal metabolite. The purpose of the study was to design and execute a synthetic strategy for leopolic acid A, which could potentially lead to the development of new antimicrobial compounds given the growing concern over antibiotic resistance. The synthesis involved crucial steps such as a Dieckmann cyclization to form the 2,3-pyrrolidinedione ring and a Wittig olefination to introduce the polymethylene chain. Key chemicals used in the process included p-methoxybenzylamine, diethyl oxalate, BnBr, K2CO3, DIBAL-H, PPh3, CBr4, n-nonanal, LiHMDS, CAN, and 2-tert-butoxycarbonylamino-3-methylbutyric acid pentafluorophenyl ester, among others. The study concluded that leopolic acid A was successfully synthesized in an 11-step process, despite the instability of several intermediates containing the 2,3-pyrrolidinedione moiety. The synthesized compounds showed antibacterial activity, suggesting their potential as promising candidates for future development in the fight against antibiotic resistance. The research also paved the way for further synthesis of analogues to build a structure–activity relationship profile and optimize the activity.