91049-51-3

Basic information

• Product Name: 2-Oxazolidinone, 3,4-dimethyl-5-phenyl-, (4R,5R)-
• CAS NO: 91049-51-3
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Mol File: 91049-51-3.mol

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3,4-dimethyl-5-phenyl-, (4R,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3,4-dimethyl-5-phenyl-, (4R,5R)-(91049-51-3)
• EPA Substance Registry System: 2-Oxazolidinone, 3,4-dimethyl-5-phenyl-, (4R,5R)-(91049-51-3)

Safety Data

• Hazardous Substances Data: 91049-51-3(Hazardous Substances Data)

Upstream product

• 75-44-5 phosgene 
• 90-82-4 rac-pseudoephedrine 
• 77-78-1 dimethyl sulfate 
• 7647-01-0 hydrogenchloride 
• 42510-95-2 N-((1RS,2RS)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-urea 
• 54418-69-8 4-methyl-5-phenyl-2-oxazolidinone 
• 74-88-4 methyl iodide 
• 100-52-7 benzaldehyde 
• 124-38-9 carbon dioxide 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 126192-86-7 (-)-(1R,2R)-(N-t-butoxycarbonyl)pseudoephedrine 
• 363620-53-5 (4R,5R)-4-(tert-butyldimethylsilyloxymethyl)-3-methyl-5-phenyl-1,3-oxazolan-2-one 
• 363620-51-3 (1R,2R)-3-(tert-butyldimethylsilyloxy)-1-methylamino-1-phenylpropan-2-ol 
• 363620-52-4 (2R,3S)-3-(tert-butyldimethylsilyloxymethyl)-1-methyl-2-phenylazirane 

Downstream Products

• 90-81-3 ephedrine 
• 1201-56-5 (+/-)-N-methylephedrine 
• 321-97-1 (1R,2R)-pseudoephedrine 

Relevant articles and documents

Catalytic activity of MCM-41-TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate

The synthesis of carbamates 3 and unsymmetrical alkyl carbonates 5 by reaction of diethyl carbonate with aliphatic amines or alcohols has been realized by using as heterogeneous catalyst a hybrid organic-inorganic material prepared by anchoring TBD to MCM-41 silica. Products are obtained in high yield and very good selectivity and the solid catalyst can be recovered simply by filtration and reused for different cycles without apparent lowering of activity. A supported N -carbethoxyguanidinium active intermediate is proposed, and some spectroscopic data are shown to support the mechanistic hypothesis.

Experimental and DEE study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism

Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and!or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the carbonyl oxygen of the Boc group to the benzylic carbon and the other one through a double SN2 process. In the erythro derivatives the first mechanism is predominant, while in the threo derivatives both mechanisms have similar energy. This hypothesis is supported by theoretical calculations and additional experimental assays.

Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations

Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such as SOCl2, TsCl, or AcCl. The intramolecular trapping of the activated carbamate by a hydroxyl group leads to the formation of 2-oxazolidinones or 2-oxazinones in good to excellent yields. This methodology was successfully applied to the synthesis of cyclic ureas up to 7-membered rings from the corresponding diamines.

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.

1,3-Heterazolidines-2-heterounsaturated compounds derived from ephedrines

Herein, a direct and easy method for preparing 2-oxo-, 2-thione- or 2-imine-1,3-heterazolidines derived from ephedrines and norephedrines are reported. The method is based on solvent free heating of ephedrines with oxocyanate or thiocyanate salts (180-200 °C). In the reactions with potassium oxocyanate in refluxing ethanol, it was possible to isolate ureidic derivatives. The structure and stereochemistry of the compounds were determined by 1H, 13C NMR, IR spectroscopies and mass spectrometry. Ureidic derivatives, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one are new compounds. Ephedrineurea, cis-1,5-dimethyl-4-phenyl-imidazolidine-2-thione and trans-4-methyl-5-phenyl-thiazolidine-2-one were also studied by X-ray diffraction.

Carboxylation and Mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent

(Equation Presented) A mild method for the synthesis of carbamates from amino alcohols involves sequential carboxylation with carbon dioxide, followed by a Mitsunobu reaction. Unexpectedly, the stereochemical course of the Mitsunobu reaction is dependent on whether the carbamic acid intermediate is N-substituted with hydrogen (retention) or carbon (inversion).

Asymmetric synthesis of (-)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

A ring-opening reaction of N-methylaziridines with Boc2O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1, derived from (2S,3S)-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4, a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions.

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.

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.