6317-31-3

Usage

Uses

Used in Pharmaceutical Industry:
3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one is used as a chiral auxiliary in asymmetric synthesis for the preparation of various chiral compounds. Its unique structure allows it to be a valuable building block for the synthesis of biologically active molecules, contributing to the development of new pharmaceuticals.
Used in Organic Reactions:
3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one is used as a catalyst in organic reactions, such as the asymmetric dihydroxylation of alkenes. Its ability to influence the stereochemistry of chemical reactions makes it a useful tool in the synthesis of enantiomerically pure compounds.
Used in Agrochemical Development:
3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one has potential applications in the development of new agrochemicals due to its ability to impact the stereochemistry of chemical reactions, which can be crucial for the synthesis of effective and selective pesticides or other agrochemical products.

Upstream product

• 75-44-5 phosgene 
• 90-82-4 rac-pseudoephedrine 
• 42510-95-2 N-((1RS,2RS)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-urea 
• 77-78-1 dimethyl sulfate 
• 17605-71-9 2-dimethylamino-1-phenyl-propan-1-ol 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 299-42-3 2-methylamino-1-phenylpropanol 
• 54418-69-8 4-methyl-5-phenyl-2-oxazolidinone 
• 74-88-4 methyl iodide 
• 100-52-7 benzaldehyde 
• 88167-98-0 4-(Diphenyl-phosphinoyl)-3,4-dimethyl-5-phenyl-oxazolidin-2-one 
• 54026-27-6 3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one 
• 90-81-3 ephedrine 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 90-81-3 ephedrine 
• 1201-56-5 (+/-)-N-methylephedrine 
• 7632-10-2 methamphetamin 
• 90-82-4 rac-pseudoephedrine 

Relevant academic research and scientific papers

Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene

The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.

Synthesis of 2-Arylethylamines by the Curtius Rearrangement

2-Arylethylamine derivatives were synthesized using the Curtius reaction and with three different methods of preparing the acyl azide functional group. Carbamates derived from isocyanate were convenient protecting groups for alkylation of amines. Starting from benzaldehyde, amphetamine was prepared in three steps through an oxazolidin-2-one intermediate in 62% overall yield. Copyright Taylor & Francis Group, LLC.

Photocycloaddition of N-acyl enamines to aldehydes and its application to the synthesis of diastereomerically pure 1,2-amino alcohols

The regio- and stereoselective synthesis of the protected cis-3- aminooxetanes cis-5 and cis-7 is reported. The oxetanes were obtained by the photocycloaddition of aliphatic (6c-e) and aromatic (4, 6a) aldehydes to the corresponding enamides (1a-d,h) or enecarbamates (1e-g). The enamine derivatives used in the Paterno-Buchi reaction were either commercially available or prepared from the corresponding acetaldehyde imines 2 by acylation. The oxetane formation proceeded with good-to-excellent simple diastereoselectivity for aromatic aldehydes (56-82% yield) and moderate selectivity for aliphatic aldehydes (46-55% yield). The cis-3-aminooxetanes are precursors for syn- and anti-1,2-amino alcohols. The relative configuration established in the photochemical step was retained upon nucleophilic ring opening between the oxygen atom and carbon atom C-4. By this means, syn-1,2-amino alcohols such as 8 and 10 were available in good yields. In contrast, the N-Boc-protected cis-3-aminooxetanes cis-5e and cis- 5f were transformed into anti-1,2-amino alcohols. Upon treatment with trifluoroacetic acid, they underwent an intramolecular nucleophilic substitution at the carbon atom C-2 of the oxetane and the oxazolidinones 11 and 12 were formed. Because the substitution occurs with inversion of configuration, anti-1,2-amino alcohols, e.g., ephedrine (15), are accessible.

Oxazolidinone penetration enhancing compounds

Compositions for carrying physiologically active agents through body membranes having the structural formula I: STR1 where: R=H, Alkyl group containing from 1-18 carbon atoms, cycloalkyl, aryl, aralkyl, alkoxy, hydroxyalkyl, alkoyloxyalkyl, acyloxyalkyl and alkoxyalkyl; X=O and NR1, where R1 is selected from H, alkyl, aralkyl acyl group containing from 1-18 carbon atoms, cycloalkyl, hydroxyalkyl, alkoyloxyalkyl acyloxyalkyl and alkoxyalkyl; Y=O and NR2, where R2 is selected from H, alkyl, aralkyl, cycloalkyl, acyl group containing from 1-18 carbon atoms, hydroxyalkyl, alkoyloxyalkyl, acyloxyalkyl and alkoxyalkyl; m=2-4; and n=0-4, are disclosed.

STEREOSELECTIVE SYNTHESIS OF (+/-)-CONHYDRINE, (+/-)-EPHEDRINE, AND (+/-)-METHYLEPHEDRINE

(+/-)-Conhydrine, (+/-)-ephedrine, and (+/-)-N-methylephedrine have been synthesized with a complete stereochemical control by utilizing carbanions in which the negative charge is located at the position α to the nitrogen atom of N-acylamines.