125133-96-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone is used as an intermediate in the synthesis of (-)-Pseudo Norephedrine (P839585), a key compound in the production of various pharmaceuticals. This intermediate plays a critical role in the development of drugs with specific therapeutic properties.
Used in the Synthesis of (-)-Pseudo Norephedrine:
(4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone is used as a precursor for the production of (-)-Pseudo Norephedrine, an enantiomer of (+)-Pseudonorephedrine (P839585). This enantiomer is a metabolite of Cathinone (C225700) and exhibits amphetamine-like stimulus properties, making it a valuable compound in the study and development of stimulant medications.
Used in Pain Management Research:
(4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone contributes to the development of (-)-Pseudonorephedrine, which has been shown to enhance the analgesic effects of Morphine (M652290). This makes it a potentially important compound in the field of pain management, as it could lead to the development of more effective treatments for chronic and acute pain.
Used in the Study of Stimulant Properties:
As a precursor to (-)-Pseudonorephedrine, (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone is indirectly involved in the study of amphetamine-like stimulant properties. This research can help in understanding the mechanisms of action of stimulant drugs and potentially lead to the development of safer and more effective medications for conditions such as ADHD and narcolepsy.

Upstream product

• 99056-06-1 C₁₀H₁₁N₃O₂ 
• 79297-23-7 (1R,2S)-2-<(ethoxycarbonyl)amino>-1-phenyl-1-propanol 
• 125453-11-4 benzyl N-(1H-benzotriazol-1-ylmethyl)carbamate 
• 141022-85-7 (4S,5R)-4-methyl-5-phenyl-3-phenylacetyloxazolidin-2-one 
• 191043-26-2 (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione 
• 492-41-1 (1R,2S)-norephedrine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 187328-75-2 (4S,5R)-3-((E)-(2R,3S)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 105-58-8 Diethyl carbonate 
• 503-38-8 trichloromethyl chloroformate 
• 20061-46-5 2-methyl-1,3-benzothiazole-5-carbaldehyde 
• 899426-20-1 (4S,5R,2'R,3'R,1''R)-3-[3'-(4-chlorophenyl)-3'-hydroxy-2'-(1''-methylsulfanyl-1''-phenylmethyl)propionyl]-4-methyl-5-phenyloxazolidin-2-one 

Downstream Products

• 54680-46-5 norephedrine 
• 42746-64-5 4r-methyl-3-nitroso-5t-phenyl-oxazolidin-2-one 
• 164913-51-3 (4S,5R)-4-methyl-3-<(2R,3S)-2-methyl-3-phenyl-3-(tosylamino)propionyl>-5-phenyloxazolidin-2-one 
• 174590-89-7 (4S,5R)-3-(5-bromovaleryl)-4-methyl-5-phenyl-2-oxazolidinone 
• 128461-58-5 (4S,5R)-4-Methyl-3-(pent-4-enoyl)-5-phenyl-1,3-oxazolidin-2-one 
• 177031-11-7 (4S,5R)-3-<3-(3,4-Dimethoxyphenyl)propanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 159563-76-5 (4S,5R)-3-Butanoyl-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 141022-85-7 (4S,5R)-4-methyl-5-phenyl-3-phenylacetyloxazolidin-2-one 
• 247038-99-9 (4S,5R)-(-)-3-(1'-oxoisovaleryl)-4-methyl-5-phenyloxazolidin-2-one 
• 260057-58-7 (3(2(2S)),4S,5R)-3-[2-((N-benzyloxycarbonyl)piperidin-2-yl)-1-oxoethyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 260057-57-6 (3(2(2R)),4S,5R)-3-[2-((N-benzyloxycarbonyl)piperidin-2-yl)-1-oxoethyl]-4-methyl-5-phenyl-2-oxazolidinone 
• 168540-62-3 (4S,5R)-3-(4-methylpentanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on 
• 329797-42-4 4-[3-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-3-oxo-propyl]-benzoic acid ethyl ester 
• 141022-84-6 (4S,5R)-4-Methyl-5-phenyl-3-(3-phenyl-propionyl)-oxazolidin-2-one 

Relevant academic research and scientific papers

Tandem copper and photoredox catalysis in photocatalytic alkene difunctionalization reactions

Oxidative alkene difunctionalization reactions are important in synthetic organic chemistry because they can install polar functional groups onto simple non-polar alkene moieties. Many of the most common methods for these reactions rely upon the reactivity of pre-oxidized electrophilic heteroatom donors that can often be unstable, explosive, or difficult to handle. Herein, we describe a method for alkene oxyamination and diamination that utilizes simple carbamate and urea groups as nucleophilic heteroatom donors. This method uses a tandem copper–photoredox catalyst system that is operationally convenient. The identity of the terminal oxidant is critical in these studies. Ag(I) salts proved to be unique in their ability to turn over the copper cocatalyst without deleteriously impacting the reactivity of the organoradical intermediates.

Remarkably efficient charcoal-promoted ring-closing carbonylations

An efficient, versatile and practical gram-scale preparation of oxazolidinone, imidazolidinone and dioxolanone is achieved. Georg Thieme Verlag Stuttgart.

Reactivity difference between diphosgene and phosgene in reaction with (2,3-anti)-3-amino-1,2-diols

In reactions of (2,3-anti)-3-amino-1,2-diols with diphosgene and phosgene and their conversion into 1,3-oxazolidin-2-ones, some differences in the stereochemistry of the reactions have been found with these two reagents. The reactions with phosgene afforded the expected cis-oxazolidinones, and in the reaction with diphosgene under the same reaction conditions, the trans-oxazolidinones were also obtained.

Stereoselective synthesis of oxazolidin-2-ones via an asymmetric aldol/curtius reaction: Concise total synthesis of (?)-cytoxazone

Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (?)-cytoxazone. Consisting of three steps, this is one of the shortest syntheses reported to date. Ultimately, this convenient platform would provide a promising method for the early phases of drug discovery.

Base Induced C-5 Epimerisation of 4-Methyl-5-phenyl Oxazolidinones: Chiral Auxiliaries Derived from Norephedrine and Norpseudoephedrine.

Treatment of cis- and trans-4-methyl-5-phenyl oxazolidinones 2 and 3 with excess butyllithium at 0 deg C results in C-5 epimerization, via a common intermediate N,C-5 dianion, generating after protonation a 1:4 mixture of 2:3.

Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes

(Chemical Equation Presented) We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate β-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction.

A novel nucleophilic attack to N-enoyl oxazolidinethiones

The oxazolidinethione synthon can act as a chiral auxiliary and nucleophile (S-) carrier molecule simultaneously. Surprisingly, the thiolate attacks N-enoyl oxazolidinethiones producing a new heterocycle, as established by X-ray analysis.

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

A new type of L-Tertiary leucine-derived ligand: Synthesis and application in Cu(II)-catalyzed asymmetric Henry reactions

A new series of Schiff bases derived from amino acids were developed as chiral ligands for Cu(II)-catalyzed asymmetric Henry reactions. The optimum ligand 7d exhibited outstanding catalytic efficiency in the Cu(II)-catalyzed asymmetric Henry additions of four nitroalkanes to different kinds of aldehydes to produce 76 desired adducts in high yields (up to 96%) with excellent enantioselectivities, up to 99% enantiomeric excess (ee).

Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions

Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.