77868-84-9

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzyl-3-bromopyrrolidin-2-one is utilized as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Research and Development:
In the realm of research and development, 1-benzyl-3-bromopyrrolidin-2-one serves as a crucial compound for exploring new drug candidates and chemical processes. Its versatility in forming different chemical structures makes it an indispensable tool for scientists working on innovative organic synthesis pathways.
Used in Organic Chemistry:
1-Benzyl-3-bromopyrrolidin-2-one is recognized for its potential as a building block in the creation of diverse chemical structures. This makes it a valuable compound in the field of organic chemistry, where it can be used to construct a wide array of complex molecules with potential applications in various industries.

Upstream product

• 100-46-9 benzylamine 
• 82820-87-9 2,4-dibromobutanoyl chloride 
• 77868-77-0 N-benzyl-2,4-dibromobutyramide 

Downstream Products

• 6837-27-0 (+/-)-1-benzyl-3-phenylpyrrolidin-2-one 
• 749200-45-1 3-amino-1-benzyl-pyrrolidin-2-one 
• 190778-54-2 3-(3'-benzyloxy-1'-propenylidene)-N-benzylpyrrolidin-2-one 
• 100372-86-9 3-acetoxy-1-benzyl-2-pyrrolidinone 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of novel pyrrolidinone small-molecule Formyl peptide receptor 2 agonists

A series of Formyl peptide receptor 2 small molecule agonists with a pyrrolidinone scaffold, derived from a combination of pharmacophore modelling and docking studies, were designed and synthesized. The GLASS (GPCR-Ligand Association) database was screened using a pharmacophore model. The most promising novel ligand structures were chosen and then tested in cellular assays (calcium mobilization and β-arrestin assays). Amongst the selected ligands, two pyrrolidinone compounds (7 and 8) turned out to be the most active. Moreover compound 7 was able to reduce the number of adherent neutrophils in a human neutrophil static adhesion assay which indicates its anti-inflammatory and proresolving properties. Further exploration and optimization of new ligands showed that heterocyclic rings, e.g. pyrazole directly connected to the pyrrolidinone scaffold, provide good stability and a boost in the agonistic activity. The compounds of most interest (7 and 30) were tested in an ERK phosphorylation assay, demonstrating selectivity towards FPR2 over FPR1. Compound 7 was examined in an in vivo mouse pharmacokinetic study. Compound 7 may be a valuable in vivo tool and help improve understanding of the role of the FPR2 receptor in the resolution of inflammation process.

Enantioconvergent Alkylations of Amines by Alkyl Electrophiles: Copper-Catalyzed Nucleophilic Substitutions of Racemic α-Halolactams by Indoles

Transition-metal catalysis has the potential to address shortcomings in the classic SN2 reaction of an amine with an alkyl electrophile, both with respect to reactivity and to enantioselectivity. In this study, we describe the development of a user-friendly method (reaction at room temperature, with commercially available catalyst components) for the enantioconvergent nucleophilic substitution of racemic secondary alkyl halides (α-iodolactams) by indoles. Mechanistic studies are consistent with the formation of a copper(I)-indolyl complex that reacts at different rates with the two enantiomers of the electrophile, which interconvert under the reaction conditions (dynamic kinetic resolution). This investigation complements earlier work on photoinduced enantioconvergent N-alkylation, supporting the premise that this important challenge can be addressed by a range of strategies.

Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.

Cobalt-Catalyzed Cross-Coupling of α-Bromo Amides with Grignard Reagents

A cobalt-catalyzed cross-coupling between α-bromo amides and Grignard reagents is disclosed. The reaction is general and allows access to a large variety of α-aryl and β,γ-unsaturated amides. Some mechanistic investigations have been undertaken to determine the nature of the intermediate species.

Chemoenzymatic enantioselective synthesis of 3-hydroxy-2-pyrrolidinones and 3-hydroxy-2-piperidinones

The enantioselective synthesis of 3-hydroxypyrrolidin-2-ones and 3-hydroxy piperidin-2-ones has been carried out in high enantiomeric excess employing immobilized lipase from Pseudomonas cepacia.

Cephalosporin derivatives

The present invention relates to compounds of formula I STR1 wherein R1 is a group selected from 2-, 3-, and 4-hydroxyphenyl, 3-nitrophenyl, and 3-fluoro-4-hydroxyphenyl; as well as readily hydroyzable esters thereof, pharmaceutically acceptabl

Synthesis of β-enaminoesters and lactams by Michael addition of N- benzylaniline to new allenic esters and lactams

The synthesis of original allenic lactams 2 and allenic esters 5 is presented and their Michael condensation with N-benzylaniline described.

Convenient Syntheses of Cyclic Carboxamides from α,β,γ,δ and ε-halocarboxamides under Phase Transfer Conditions

Piperazine-2,5-diones (2) were prepared by N-alkylation between two molecules of α-halocarboxamides (1) in the presence of a phase transfer catalyst in yields of 64-88percent. β,γ,δ and ε-Lactams (6,9 and 13) were similarly synthesized by intramolecular N-alkylation of the corresponding halocarboxamides (5, 8 and 12) under phase transfer conditions in 53-99percent yields.Keywords--piperazine-2,5-dione; β-lactam; γ, δ, and ε lactams; bis-β-lactam; phase transfer catalyst; intramolecular N-alkylation

CONVENIENT SYNTHESES OF PIPERAZINE-2,5-DIONES AND LACTAMS FROM HALOCARBOXAMIDES USING PHASE TRANSFER CATALYSTS

Inter- and intramolecular N-alkylation of α-halocarboxamides and dihalocarboxamides in the presence of solid phase transfer catalyst led to the corresponding piperazine-2,5-diones (2) and lactams (4) in the yields of 64-88 and 63-99 percent, respectively.A one-pot synthesis of β-lactams (7) from α-methyl-α,β-dibromopropionyl chloride (5) and α-amino acid using phase transfer catalyst was also successfully achieved.