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Usage

Uses

Used in Pharmaceutical Industry:
2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4R)is used as a key intermediate in the synthesis of various pharmaceuticals and drugs. Its unique chiral structure and the presence of the 4-chlorophenyl group allow it to impart specific pharmacological activities or biological effects when incorporated into drug molecules, enhancing their therapeutic potential.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4R)serves as a valuable building block for the development of novel biologically active compounds. Researchers can utilize its unique structural features to design and synthesize new drug candidates with improved efficacy, selectivity, and safety profiles.
Used in Drug Optimization:
2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4R)can be employed in the optimization of existing drug molecules. By incorporating this chiral compound into the drug's structure, chemists can potentially enhance the drug's pharmacokinetic and pharmacodynamic properties, leading to improved therapeutic outcomes.
Used in Chiral Synthesis:
As a chiral compound, 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4R)is an important reagent in chiral synthesis. It can be used to prepare enantiomerically pure compounds, which are essential in various applications, including the development of enantioselective catalysts and the synthesis of chiral pharmaceuticals.

Upstream product

• 321575-57-9 (R)-phenyl 3-(4-chlorophenyl)-4-nitrobutanoate 
• 537676-63-4 ethyl (3R)-3-cyano-3-(4-chlorophenyl)propanoate 
• 537676-64-5 ethyl 4-azido-3-(4-chlorophenyl)-2-butenoate 
• 143-33-9 sodium cyanide 
• 141545-22-4 (R)-3-hydroxy-3-(4-chlorophenyl)-propionic acid ethyl ester 
• 153805-70-0 (Z)-ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate 
• 101671-01-6 1-nitro-2-(4-chlorophenyl)ethylene 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 761434-42-8 (R)(-)-2-[1-(4-chlorophenyl)-2-nitroethyl]malonic acid dimethyl ester 
• 1256161-69-9 methyl (4R)-4-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylate 
• 140-53-4 p-chlorobenzyl cyanide 
• 537676-65-6 ethyl (3S)-3-bromo-3-(4-chlorophenyl)propanoate 
• 1006386-92-0 ethyl (2S,3S)-2-bromo-3-hydroxy-3-(4-chlorophenyl)propanoate 
• 1006386-91-9 (4R,5S)-4-carbethoxy-5-(4-chlorophenyl)-1,3,2-dioxathiolane 2-oxide 

Downstream Products

• 63701-55-3 (R)-(-)-baclofen hydrochloride 
• 63701-56-4 (+)-Baclofen hydrochloride 
• 1252761-51-5 (R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one 
• 69308-37-8 (R)-baclofen 
• 1252761-94-6 tert-butyl (R)-4-(4-chloro-3-iodophenyl)-2-oxopyrrolidine-1-carboxylate 
• 1345248-90-9 C₁₇H₁₉ClN₂O₃ 
• 1252763-20-4 (3R)-3-[3-((1R)-1-(4-pyridyl)ethoxy)-4-chlorophenyl]-4-aminobutanoic acid 
• 1252763-01-1 (R)-4-amino-3-(4-chloro-3-(pyridin-4-ylmethoxy)phenyl)butanoic acid 
• 1345248-84-1 C₁₇H₁₈ClNO₃ 

Relevant academic research and scientific papers

Enantioselective conjugate hydrocyanation of α,β-unsaturated N-acylpyrroles catalyzed by chiral lithium(I) phosphoryl phenoxide

Enantioselective conjugate hydrocyanation of α,β-unsaturated N-acylpyrroles with the combined use of Me3SiCN, LiCN, and HCN has been developed in the presence of a chiral lithium(I) phosphoryl phenoxide catalyst. This reaction is useful for a v

Michael addition of nitromethane to non-racemic chiral Cr(CO)3 complexes of ethyl cinnamate derivatives: Stereoselective synthesis of (R)-(-)-baclofen

We carried out a highly stereoselective Michael addition (96% de) of nitromethane to enantiomerically pure tricarbonyl(ethyl-4-chloro-2-trimethylsilylcinnamate)chromium(0). This reaction is the key step in the synthesis of (R)-(-)-baclofen, a potent antispastic drug. Copyright (C) 2000 Elsevier Science Ltd.

Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation

A Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system has been identified for the straightforward asymmetric synthesis of chiral γ-lactams. A variety of NH free α,β-unsaturated lactams bearing a β-aryl or β-alkyl substituent were smoothly hydrogenated to

Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position

With the assistance of hydrogen bonds, the first asymmetric hydrogenation of β-cyanocinnamic esters is developed, affording chiral β-cyano esters with excellent enantioselectivities (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral GABA-derivatives such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with a single H-bond donor performs better than that with double H-bond donors, which is a novel discovery in the metalorganocatalysis area.

Synthesis and Evaluation of a New 18F-Labeled Radiotracer for Studying the GABAB Receptor in the Mouse Brain

New GABAB agonists, fluoropyridyl ether analogues of baclofen, have been synthesized as potential PET radiotracers. The compound with highest inhibition binding affinity as well as greatest agonist response, (R)-4-amino-3-(4-chloro-3-((2-fluoro

Squaramide-Catalyzed Michael Addition as a Key Step for the Direct Synthesis of GABAergic Drugs

Enantioselective organocatalytic Michael additions serve as the key step in syntheses of chiral drugs based on γ-aminobutyric acid. The applicability of various squaramide catalysts for these Michael-type reactions has been assessed. Very good results in

A synthetic γ-amino butyric acid kind of chiral the method for preparing the compound of

The invention discloses a method for synthesizing a gamma-aminobutyric acid chiral compound. The method comprises the following steps of: adding nitroolefin and malonate to a solvent in the presence of a catalyst A and an additive; carrying out conjugate

Opposite enantioselectivity in the bioreduction of (Z)-β-aryl-β-cyanoacrylates mediated by the tryptophan 116 mutants of old yellow enzyme 1: Synthetic approach to (R)- and (S)-β-aryl-γ-lactams

The Trp 116 mutants of Old Yellow Enzyme 1 that catalyse the reduction of (Z)-β-aryl-β-cyanoacrylates give the opposite enantioselectivity according to the nature of the amino acid in position 116. Small amino acids (e.g., alanine) make the substrate bind

Efficient synthesis of β-aryl-γ-lactams and their resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.

Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: An organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent

An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions γ-nitro-β-aryl-α-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABAB receptor agonist baclofen.