313352-62-4

Usage

Uses

Used in Chemical Synthesis:
(5R)-5-phenyl-2-Pyrrolidinone is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of complex organic molecules.
Used in Pharmaceutical Industry:
(5R)-5-phenyl-2-Pyrrolidinone is used as a building block for the production of biologically active compounds, leveraging its unique structure to create new pharmaceutical agents with potential therapeutic applications.
Used in Medicinal Chemistry:
(5R)-5-phenyl-2-Pyrrolidinone is utilized in the field of medicinal chemistry for its potential to be incorporated into drug molecules, enhancing their efficacy and selectivity in targeting specific biological pathways.

Upstream product

• 948018-51-7 methyl (R)-5-[(3,5-dimethyl-4-methoxyphenyl)amino]-4-phenylbutanoate 
• 23132-29-8 4-oxo-4-phenylbutanamide 
• 55666-45-0 4-oxo-4-phenyl-butyric acid tert-butyl ester 
• 104750-69-8 isopropyl 4-phenyl-4-oxobutanoate 
• 6270-17-3 ethyl 3-benzoylpropanoate 
• 2051-95-8 succinylbenzene 
• 32153-46-1 4-PBHA 
• 18496-54-3 phenylbutyric acid chloride 
• 1821-12-1 4-Phenylbutyric acid 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 22050-10-8 (+/-)-5-phenyl-2-pyrrolidinone 
• 100-58-3 phenylmagnesium bromide 
• 100-52-7 benzaldehyde 
• 111636-13-6 4-hydroxy-4-phenyl-butyric acid ethyl ester 

Downstream Products

• 56523-47-8 (R)-2-phenylpyrrolidine 
• 23132-29-8 4-oxo-4-phenylbutanamide 

Relevant academic research and scientific papers

Method for synthesizing chiral lactam through tandem reductive amination

The invention belongs to the technical field of chemical synthesis preparation, and particularly relates to a method for synthesizing chiral lactam through tandem reductive amination, which successfully realizes ruthenium-catalyzed asymmetric reductive amination/cyclization tandem reaction to efficiently construct chiral lactam by using substrates of keto acid and keto ester.

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.

Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions

While remarkable progress has been made over the past decade, new design strategies for chiral catalysts in enantioselective C(sp3)-H functionalization reactions are still highly desirable. In particular, the ability to use attractive noncovalent interactions for rate acceleration and enantiocontrol would significantly expand the current arsenal for asymmetric metal catalysis. Herein, we report the development of a highly enantioselective Ir(III)-catalyzed intramolecular C(sp3)-H amidation reaction of dioxazolone substrates for synthesis of optically enriched γ-lactams using a newly designed α-amino-acid-based chiral ligand. This Ir-catalyzed reaction proceeds with excellent efficiency and with outstanding enantioselectivity for both activated and unactivated alkyl C(sp3)-H bonds under very mild conditions. It offers the first general route for asymmetric synthesis of γ-alkyl γ-lactams. Water was found to be a unique cosolvent to achieve excellent enantioselectivity for γ-aryl lactam production. Mechanistic studies revealed that the ligands form a well-defined groove-type chiral pocket around the Ir center. The hydrophobic effect of this pocket allows facile stereocontrolled binding of substrates in polar or aqueous media. Instead of capitalizing on steric repulsions as in the conventional approaches, this new Ir catalyst operates through an unprecedented enantiocontrol mechanism for intramolecular nitrenoid C-H insertion featuring multiple attractive noncovalent interactions.

Ruthenium(II)-Catalyzed Enantioselective γ-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-ones

We report the Ru-catalyzed enantioselective annulation of 1,4,2-dioxazol-5-ones to furnish γ-lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C - H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- and enantioselectivities; the competing Curtius-type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C - H bonds was also achieved with remarkable tolerance to the C=C and C=C bonds.

Amino acid chiral ligand containing bidentate coordination group, chiral catalyst, and corresponding preparation methods and applications thereof

The present invention relates to an amino acid chiral ligand containing a bidentate coordination group, a chiral catalyst, and corresponding preparation methods and applications thereof. The chiral ligand is prepared from a cheap and easily available amino acid, and the development of the chiral ligand can improve the diversity of the chiral ligand. The chiral Ir (III) catalyst is simply and efficiently prepared from the chiral ligand only through a one-step reaction. The chiral Ir (III) catalyst is characterized in that a bidentate guiding group is introduced to an amino acid framework to change the original coordination mode of the amino acid and Ir in order to enhance the chiral control ability of the amino acid to the Ir(III) catalyst. The chiral Ir(III) catalyst is designed and synthesized for the first time, and the selectivity reaches up to 99% ee when the catalyst is successfully applied to the high-efficiency asymmetric synthesis of chiral gamma-cyclolactam, so the catalyst has superior stereo control ability.

Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones

We report the Ru-Catalyzed enantioselective annulation of 1,4,2-Dioxazol-5-Ones to furnish ?-Lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-Withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- A nd enantioselectivities; the competing Curtius-Type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the Ca?C and Ca‰iC bonds.

Non- C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)-H Amidation

A new class of chiral ruthenium catalysts is introduced in which ruthenium is cyclometalated by two 7-methyl-1,7-phenanthrolinium heterocycles, resulting in chelating pyridylidene remote N-heterocyclic carbene ligands (rNHCs). The overall chirality results from a stereogenic metal center featuring either a or Δabsolute configuration. This work features the importance of the relative metal-centered stereochemistry. Only the non-C2-symmetric chiral-at-ruthenium complexes display unprecedented catalytic activity for the intramolecular C(sp3)-H amidation of 1,4,2-dioxazol-5-ones to provide chiral -lactams with up to 99:1 er and catalyst loadings down to 0.005 mol % (up to 11 ?200 TON), while the C2-symmetric diastereomer favors an undesired Curtius-type rearrangement. DFT calculations elucidate the origins of the superior C-H amidation reactivity displayed by the non-C2-symmetric catalysts compared to related C2-symmetric counterparts.

Conversion of γ- and δ-Keto Esters into Optically Active Lactams. Transaminases in Cascade Processes

A one-pot two-step enzymatic strategy has been designed for the production of optically active γ- and δ-lactams in aqueous medium under mild conditions. The approach is based on the biotransamination of ethyl or methyl keto esters bearing different alkyl or aryl substitution patterns at α-position to the ketone functionality. In this manner, the keto esters were transformed into the corresponding amino esters with excellent conversions, which underwent spontaneous cyclisation in the reaction medium without addition of external reagents. Depending on the transaminase selectivity, both lactam enantiomers can be obtained, so initial enzyme screenings were performed using commercially available and made in house enzymes. Reaction conditions were optimised focusing on the substrate concentration, temperature and ratio of amine donor vs acceptor. Thus, ten γ- and δ-lactams were obtained in good to high isolated yields (70–90%) and excellent selectivities (94–99%) after one or two days at 30 or 45 °C. (Figure presented.).

Synthesis of Chiral γ-Lactams via in Situ Elimination/Iridium-Catalyzed Asymmetric Hydrogenation of Racemic γ-Hydroxy γ-Lactams

Chiral γ-lactams have been synthesized in excellent yields and enantioselectivities (up to 99% yield and 96% ee) from easily accessible racemic γ-hydroxy γ-lactams via an iridium-phosphoramidite catalyzed asymmetric hydrogenation. The reaction was designed based on insight into the reaction mechanism demonstrated in previous work and can be carried out at a reduced catalyst loading of 0.1 mol % on a gram scale. Several potential bioactive compounds can be synthesized from the reduced products. Mechanistic studies indicated that the reduced products were obtained via the hydrogenation of the N-acyliminium cations, generated from γ-hydroxy γ-lactams.

TRICYCLIC MODULATORS OF TNF SIGNALING

The invention provides tricyclic heterocyclic compounds, pharmaceutically acceptable salts, prodrugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the invention may be useful for treating immunological and oncological conditions.