39263-91-7

Upstream product

• 90-82-4 pseudoephedrine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 35026-77-8 (S)-2-(dimethylamino)propiophenone 
• 66574-19-4 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidine 
• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 15351-09-4 metamfepramone 
• 6084-17-9 2-chloro-1-phenylpropan-1-one 
• 299-42-3 (R,R)-(-)-pseudoephedrine 
• 67-68-5 dimethyl sulfoxide 
• 93-55-0 1-phenyl-propan-1-one 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 130459-53-9 (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol 

Downstream Products

• 57155-63-2 (+)-(1S,2S)-N-dodecyl-N,N-dimethylpseudoephedrinium bromide 
• 158837-63-9 (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane 
• 129216-60-0 lithium N-methylpseudoephedrate 
• 74059-55-5 (1S,2S)-N-methyl-ψ-ephedrine propionate 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 4436-22-0 (2S,3R)-2-methyl-3-phenyloxirane 
• 158837-61-7 O-<(1S,2S)-N-Methylephedrine>-N,N'-diisopropylisourea 
• 942-45-0 (1S,2S)-β-chloro-N,N',α-trimethylbenzeneethanammonium chloride 
• 445298-95-3 (S,S)-N-methylpseudoephedrine α-bromo-α-methylacetate 
• 445298-98-6 (S,S)-N-methylpseudoephedrine α-bromo-α-ethylacetate 
• 445298-99-7 (S,S)-N-methylpseudoephedrine α-bromo-α-n-butylacetate 
• 479350-68-0 (S,S)-N-methylpseudoephedrine 2-bromo-4-phenylbutanoate 

Relevant academic research and scientific papers

THE HIGHLY STEREOSELECTIVE CONVERSION OF N,N-DIMETHYLAMPHETAMINE INTO N-METHYLPSEUDOEPHEDRINE; A MIMIC OF THE ENZYME MEDIATED STEREOSPECIFIC BENZYLIC HYDROXYLATION OF 2-ARYLETHYLAMINES

Treatment of (S)-(η6-N,N-dimethylamphetamine)Cr(CO)3, with n-butyllithium below -40 deg C gives a stable benzylic carbanion via loss of the pro-R-benzylic proton.Warming of this anion above -40 deg C gives (η6-E-β-methylstyrene)Cr(CO), via an ElcB type elimination wilhst trapping with an electrophile below -40 deg C gives benzylically functionalised amphetamines with overall retention of configuration.The use of oxodiperoxymolybdenum(pyridine)hexamtehylphosphoramide as the electrophile gives optically pure (1S,2S)-N-methylpseudoephedrine after decomplexation.

Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution

The iridium-f-amphox-catalyzed asymmetric hydrogenation of racemic α-amino β-unfunctionalized ketones proceeds via a DKR (dynamic kinetic resolution) process for the construction of various chiral N,N-disubstituted α-amino β-unfunctionalized alcohols in quantitative yields with excellent enantioselectivities and diastereoselectivities (all products >99% ee and >99:1 dr, TON up to 100 000). Importantly, this catalytic asymmetric hydrogenation with a DKR process provided a highly efficient and powerful synthetic strategy for the preparation of key chiral intermediates of the preclinical antitumor agent (S,S)-R116010.

Ephedrine- and pseudoephedrine-derived thioureas in asymmetric michael additions of keto esters and diketones to nitroalkenes

Ephedrine-derived bifunctional thioureas have been synthesized and applied as organocatalysts in Michael additions of 1,3-dicarbonyl compounds to nitroalkenes. Georg Thieme Verlag Stuttgart.

1,2-Aminothioethers Derived from Ephedrine and Pseudoephedrine: Heterobidentate Ligands for the Palladium-Catalysed Asymmetric Allylic Substitution Reaction

Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89 percent. The stereoelectronic effects operating in the reactions are discussed.

Dynamic resolution of α-bromo-α-alkyl esters using N-methyl pseudoephedrine as a chiral auxiliary: Asymmetric syntheses of α-amino acid derivatives

N-Methyl pseudoephedrine mediated dynamic resolution of α-bromo-α-alkyl esters in nucleophilic substitution reaction has been investigated. Best results are obtained when α-bromo-α-alkyl esters 1, 4 and 5 are allowed to equilibrate before the addition of nucleophile. This simple epimerization-substitution sequence provides a practical protocol for asymmetric syntheses of α-amino acid derivatives 2, 7 and 8 up to 98:2 enantiomeric ratio.

Facile inversion of configuration of N-Boc-β-aminoalcohols via S(N)2 cyclization to oxazolidinones

Oxazolidinones are obtained by the cyclization of mesylates derived from N-Boc-β-Aminoalcohols. Hydrolysis of the N-Boc-Oxazolidinones regenerates the protected aminoalcohols with inverted configuration at the hydroxy group. (C) 2000 Elsevier Science Ltd.

The Reductive Cleavage of Cyclic Aminol Ethers to N,N-Dialkylamino-derivatives: Modifications to the Eschweiler-Clarke Procedure

The reductive cleavage of cyclic aminol ethers to give N-alkylamino-derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.

Reaction of alkyl sulfoxides and phenylphosphinic acid with amines. Alternative reagents for secondary amines N-alkylation

Phenylphosphinic acid and dialkylsulfoxides are found to be alternative reagents for respectively the reducing reagent (formic acid) and the alkylating reagent (aldehyde) currently used for secondary amines N-alkylation. Primary amines do not react with this system, but phenylglycine is decarboxilated to benzylamine.

AUXILIARY SRTUCTURE AND ASYMMETRIC INDUCTION IN THE "MUKAIYAMA-ALDOL" REACTIONS OF CHIRAL SILYL KETENE ACETALS

A variety of chiral auxiliaries R*OH were prepared and tested for levels of asymmetric induction control in the "Mukaiyama-aldol" reaction of chiral silyl ketene acetals.Structural features required for high levels of control are discussed.

Fluoride Ion Catalyzed Reduction of Aldehydes and Ketones with Hydrosilanes. Synthetic and Mechanistic Aspects and an Application to the Threo-Directed Reduction of α-Substituted Alkanones

Reduction of aldehydes and ketones with hydrosilanes proceeded in the presence of a catalytic amount of tetrabutylammonium fluoride or tris(diethylamino)sulfonium difluorotrimethylsilicate in aprotic polar solvents under mild conditions.A significant isotope effect (kH/kD = 1.50) was observed in competitive reduction of acetophenone with HSiMe2Ph and DSiMe2Ph.The reaction was of first order in the concentration of an aprotic polar solvent HMPA.Reduction of 2-methylcyclohexanone gave cis-2-methylcyclohexanol with selectivities up to 95percent.The kinetic and stereochemical results suggest that a hexavalent fluorosilicate - is involved. α-Alkoxy (acyloxy or dimethylamino) ketones were transformed to threo alcohols in high diastereoselectivities.The reduction was also applied to α-methyl-β-keto amides, RCOCH(MeCONR)2, to afford the corresponding threo alcohols in >98percent selectivity.The threo selectivity is explained in terms of the Felkin-Anh model in which interaction of carbonyl oxygen with a countercation is ideally suppressed.The threo-directed reduction was applied to (R)-1-phenyl-4-(2-tetrahydropyranyloxy)-1-penten-3-one and N-(2-benzoylpropanoyl)piperidine.The resulting threo alcohols were respectively converted into (2R,3S)-2,3-(cyclohexylidenedioxy)butanal, a key intermediate of daunosamine synthesis, and into a pharmacologically useful compound threo-N-(3-hydroxy-2-methyl-3-phenylpropyl)piperidine.