125133-96-2

Basic information

• Product Name: (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone
• Synonyms: (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone
• CAS NO: 125133-96-2
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.19984
• Mol File: 125133-96-2.mol
• Article Data: 44

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone(125133-96-2)
• EPA Substance Registry System: (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone(125133-96-2)

Safety Data

• Hazardous Substances Data: 125133-96-2(Hazardous Substances Data)

Usage

Description

(4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone is a chiral heterocyclic compound featuring a methyl and phenyl substituent on a 2-oxazolidinone ring. It is characterized by its specific (4R,5R) stereochemistry, which is crucial for its applications in the synthesis of pharmaceutical compounds.

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

• 637-50-3 1-phenylpropene 
• 4248-19-5 tert-butyl carbazate 
• 104863-92-5 (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol 
• 191043-26-2 (4S,5R)-4-methyl-5-phenyl-1,3-oxazolidine-2-thione 
• 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 
• 492-41-1 (1R,2S)-norephedrine 
• 105-58-8 Diethyl carbonate 
• 102-09-0 bis(phenyl) carbonate 
• 48115-38-4 norepinephrine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 37577-07-4 Norpseudoephedrine 
• 959628-18-3 2-methyl-3-phenyloxirane-2-carbaldehyde 

Downstream Products

• 54680-46-5 norephedrine 
• 42746-64-5 4r-methyl-3-nitroso-5t-phenyl-oxazolidin-2-one 
• 130258-52-5 (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 142956-08-9 (4S,5R)-3-(3,3-Diphenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 147900-34-3 (4S,5R)-3-(2-5H-Dibenzo[a,d]cyclohepten-5-yl-acetyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 157555-77-6 (4S,5R)-3-<(S)-2,2-dimethyl-1,3-dioxolane-4-propanoyl>-4-methyl-5-phenyl-2-oxazolidinone 
• 321-97-1 (1R,2R)-pseudoephedrine 
• 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 
• 177031-10-6 (4S,5R)-3-(3-Carboxypropanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 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 
• 77877-20-4 (4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one 
• 202932-15-8 (4S,5R)-3-[2-(4-Benzyloxy-phenyl)-acetyl]-4-methyl-5-phenyl-oxazolidin-2-one 

Relevant articles and documents

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.

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.

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.

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.

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).