90-82-4

Usage

Environmental Fate

Through use as a decongestant and production, release to the environment may result from various waste streams. Pseudoephedrine is also found in plants in the genus Ephedra (Ephedraceae) otherwise known as Ma Huang. It has a vapor pressure of 8.3×104 mm Hg at 25 °C and if released into air it will exist both as vapor and in particulate phase in the atmosphere. Vapor-phase pseudoephedrine will be degraded by reactions with hydroxyl radicals, which are photochemically produced. The half-life for this reaction is estimated at 4 h. Particulate-phase pseudoephedrine will be removed from the atmosphere by wet and dry deposition. Pseudoephedrine is not susceptible to direct photolysis by sunlight. Based upon an estimated Koc of 73, pseudoephedrine is expected to have a high mobility in soil. The pKa of 10.25 indicates that it will exist primarily in the cation form in the environment and it will absorb more strongly to soil containing clay or organic carbon.

Purification Methods

Crystallise the amine from dry diethyl ether, or from water and dry it in a vacuum desiccator. [Beilstein 13 IV 1878.]

Toxicity evaluation

Pseudoephedrine is a weak base (pKa, 9.4) that stimulates both α- and β-adrenergic receptors, as well as causing the release of neuronal norepinephrine. This mixed α/β adrenergic stimulation produces both hypertension and tachycardia, as opposed to the hypertension with reflex bradycardia seen with selective a agonists.

InChI:InChI=1/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1

Upstream product

• 87-69-4 L-Tartaric acid 
• 90-82-4 rac-pseudoephedrine 
• 16735-30-1 (S)-2-(benzyl-methyl-amino)-1-phenyl-propan-1-one 
• 133160-98-2 4-nitro-benzoic acid-[((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide] 
• 127-09-3 sodium acetate 
• 94133-42-3 (+)-Chloroephedine hydrochloride 
• 16413-75-5 1-(Phenyl)-2-(N-methyl-N-acetylamino)-1-propanol 
• 74-88-4 methyl iodide 
• 79219-15-1 (S)-2-<(ethoxycarbonyl)amino>-1-phenyl-1-propanone 
• 33574-02-6 cyclopropylmethyl iodide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 170115-96-5 2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide 
• 52289-93-7 o-Methoxybenzyl bromide 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 

Downstream Products

• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 41958-41-2 (+)-N-o-toluoyl-pseudoephedrine 
• 90-82-4 rac-pseudoephedrine 
• 90-81-3 ephedrine 
• 537-46-2 Methamphetamin 
• 299-42-3 ephedrine 
• 103397-84-8 bis-((1Ξ,2S)-2-methylamino-1-phenyl-propyl)-ether 
• 42511-08-0 (+)-hexahydro-pseudoephedrine 
• 36298-43-8 3,4-dimethyl-2,5-diphenyl-oxazolidine 
• 123049-92-3 (2S)-3t,4-dimethyl-2r-phenyl-1-oxa-4-aza-spiro[4.5]decane 
• 84472-25-3 (1S,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid 
• 108131-99-3 ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamic acid-(2-hydroxy-ethyl ester); N-anilinothioformyl-(+)-pseudoephedrine 
• 41958-45-6 4-nitro-benzoic acid-[((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide]; N-(4-nitro-benzoyl)-(+)-pseudoephedrine 
• 51018-30-5 (4S)-2,2,3,4r-tetramethyl-5t-phenyl-oxazolidine 

Relevant academic research and scientific papers

Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media

Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2

In the last decade, manganese(II) complexes with N-donor tetradentate aminopyridine ligands emerged as efficient catalysts of enantioselective epoxidation of olefins and direct selective oxidation of C?H groups in complex organic molecules, with environmentally benign oxidant hydrogen peroxide. In this personal account, we summarize the progress of these catalysts with regard to ligands design, structure-reactivity correlations, evaluation of the substrate scope, as well as mechanistic studies, shedding light on the nature of active sites and the mechanisms of selective oxygenations. Several practically promising catalytic syntheses with the aid of Mn aminopyridine catalysts are exemplified.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Unlocking the potential of phenacyl protecting groups: CO2-based formation and photocatalytic release of caged amines

Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples.

POLYMORPHIC AND AMORPHOUS FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE

Disclosed herein are polymorphic and amorphous forms of anhydrate, hydrate, and solvates of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide and methods of using such compositions for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging. Further disclosed are methods of making such polymorphic and amorphous forms.

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.

Stereocontrolled alkylative construction of quaternary carbon centers

Protocols for the stereodefined formation of α,α-disubstituted enolates of pseudoephedrine amides are presented followed by the implementation of these in diastereoselective alkylation reactions. Direct alkylation of α,α-disubstituted pseudoephedrine amide substrates is demonstrated to be both efficient and diastereoselective across a range of substrates, as exemplified by alkylation of the diastereomeric pseudoephedrine α-methylbutyramides, where both substrates are found to undergo stereospecific replacement of the α-C-H bond with α-C-alkyl, with retention of stereochemistry. This is shown to arise by sequential stereospecific enolization and alkylation reactions, with the alkyl halide attacking a common π-face of the E- and Z-enolates, proposed to be opposite the pseudoephedrine alkoxide side chain. Pseudoephedrine α-phenylbutyramides are found to undergo highly stereoselective but not stereospecific α-alkylation reactions, which evidence suggests is due to facile enolate isomerization. Also, we show that α,α-disubstituted pseudoephedrine amide enolates can be generated in a highly stereocontrolled fashion by conjugate addition of an alkyllithium reagent to the s-cis-conformer of an α-alkyl-α,β-unsaturated pseudoephedrine amide, providing α,α-disubstituted enolate substrates that undergo alkylation in the same sense as those formed by direct deprotonation. Methods are presented to transform the α-quaternary pseudoephedrine amide products into optically active carboxylic acids, ketones, primary alcohols, and aldehydes. Copyright

Novel lincomycin derivatives possessing antibacterial activity

Novel lincomycin derivatives are disclosed. These lincomycin derivatives exhibit antibacterial activity. The compounds of the subject invention may exhibit potent activities against bacteria, including Gram positive organisms, and may be useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

Nonracemic α-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes

(Chemical Equation Presented) The asymmetric propargylboration of aldehydes at -78°C in 98% ee). The reagents 1 are easily prepared in both enantiomeric forms with a simple Grignard procedure and air-stable borinate complexes 2. The ozonolysis of 6 proceeds smoothly through an acylsilane intermediate to give a TMS ester, which is hydrolyzed to the α-hydroxy acid quantitatively with water.

Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols

Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt 3BH or Li(S-Bu)3BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β- aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations.