71657-88-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-4-Phenylpyrrolidin-2-one is used as a key precursor in the synthesis of pharmaceuticals and bioactive compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Chemistry:
(R)-4-Phenylpyrrolidin-2-one serves as an important intermediate in the production of various organic compounds. Its presence in chemical reactions can lead to the formation of complex molecules with diverse applications.
Used in Drug Development:
Due to its potential pharmacological properties, (R)-4-Phenylpyrrolidin-2-one is utilized in drug development for the creation of novel therapeutic agents. Its chiral nature and structural features make it a valuable building block in the design and synthesis of new drugs.

Upstream product

• 135056-44-9 (αR,4R)-1-(1'-phenylethyl)-4-phenylpyrrolidin-2-one 
• 138782-42-0 (3R,4R)-N-<(1R)-2-Hydroxy-1-phenylethyl>-2-oxo-4-phenylpyrrolidine-3-carboxamide 
• 67-56-1 methanol 
• 52950-37-5 (R)-4-amino-3-phenylbutanoioc acid hydrochloride 
• 894421-56-8 (Z)-ethyl 4-azido-3-phenylbut-2-enoate 
• 836598-15-3 (3S)-3-cyano-3-phenyl-1-pyrrol-1-ylpropan-1-one 
• 21133-98-2 ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate 
• 957770-71-7 (3R)-4-methoxyphenyl 4-nitro-3-phenylbutanethioate 
• 1402129-56-9 n-butyl 3(R)-4-amino-3-phenylbutyrate 
• 1387576-65-9 (R)-methyl 3-cyano-3-phenylpropanoate 
• 773148-47-3 methyl (R)-2-methoxycarbonyl-4-nitro-3-phenylbutanoate 
• 478369-32-3 N-bis(trimethylsilyl)-N-(phenethyl)-α-methoxycarbonyl-α-diazoacetamide 
• 98-80-6 phenylboronic acid 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 

Downstream Products

• 128372-78-1 (+)-(R)-1-tert-Butoxycarbonyl-4-phenyl-2-pyrrolidinone 
• 61586-46-7 (-)-(R)-3-Phenylpyrrolidine 
• 949925-06-8 ethyl [(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetate 
• 1437789-57-5 C₂₆H₂₁N₃O₂ 
• 949925-07-9 2-[(4R)-2-oxo-4-phenylpyrrolidin-1-yl]acetamide 
• 52950-37-5 (R)-4-amino-3-phenylbutanoioc acid hydrochloride 
• 1078-21-3 (R)-Phenibut 

Relevant academic research and scientific papers

Enantioselective conjugate addition of an α,α-dithioacetonitrile with nitroalkenes using chiral bis(imidazoline)-Pd complexes

The enantioselective conjugate addition reaction of an α,α-dithioacetonitrile with nitroalkenes was catalysed by chiral bis(imidazoline)-palladium pincer-type complexes. The reaction was applicable to various nitroalkenes to afford products in good yield with high enantioselectivity. The obtained products can be converted to γ-lactam and biologically active rolipram.

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams

Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.

Substituted 1-methyl-4-phenylpyrrolidin-2-ones – Fragment-based design of N-methylpyrrolidone-derived bromodomain inhibitors

N-Methylpyrrolidone is one of several chemotypes that have been described as a mimetic of acetyl-lysine in the development of bromodomain inhibitors. In this paper, we describe the synthesis of a 4-phenyl substituted analogue – 1-methyl-4-phenylpyrrolidin-2-one – and the use of aryl substitution reactions as a divergent route for derivatives. Ultimately, this has led to structurally complex, chiral compounds with progressively improved affinity as inhibitors of bromodomain-containing protein 4.

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.

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

COMPOUND, MANUFACTURING METHOD OF COMPOUND THROUGH ASYMMETRIC MICHAEL ADDITION USING THE COMPOUND AND MANUFACTURING METHOD OF PHENIBUT USING THE COMPOUND

The present invention relates to a compound, a method of producing compounds through an asymmetric Michael addition reaction by using the same, and a method of producing a phenibut compound. Specifically, the compound of the present invention is represented by chemical formula 1. In the chemical formula 1: L represents #AAA# or #BBB# (wherein X represents sulfur or oxygen); R_1 represents hydrogen, an alkyl group having 1-5 carbons, an aryl group having 6-12 carbon atoms, or a benzyl group; R_2 represents an aryl group having 6-12 carbon atoms; R_3 represents hydrogen or an aryl group having 1-12 carbon atoms; and hydrogen in R_1, R_2, and R_3 may be each independently substituted by an alkyl group having 1-5 carbon atoms.COPYRIGHT KIPO 2018

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

L -Proline Derived Bifunctional Organocatalysts: Enantioselective Michael Addition of Dithiomalonates to trans-β-Nitroolefins

A series of novel l-proline derived tertiary amine bifunctional organocatalysts 9 are reported, which were applied to the asymmetric Michael addition of dithiomalonates 2 to trans-β-nitroolefins 1. The reaction proceeded in high yields (up to 99%) with high enantioselectivities (up to 97% ee). The synthetic utility of this methodology was demonstrated in the short synthesis of (R)-phenibut in high yield.

BENZAMIDE CGRP RECEPTOR ANTAGONISTS

The present invention is directed to benzamide compounds which are antagonists of CGRP receptors and useful in the treatment or prevention of diseases in which CGRP is involved, such as migraine. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which CGRP is involved.

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