1201-56-5

Upstream product

• 90-82-4 pseudoephedrine 
• 74-88-4 methyl iodide 
• 35026-77-8 (S)-2-(dimethylamino)propiophenone 
• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 50-00-0 formaldehyd 
• 15351-09-4 metamfepramone 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 6317-31-3 (4RS,5SR)-3,4-dimethyl-5-phenyloxazolidin-2-one 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 54026-27-6 3-Methyl-4-methyl-5-phenyl-4-oxazolin-2-one 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 299-42-3 (R,R)-(-)-pseudoephedrine 

Downstream Products

• 57155-63-2 (+)-(1S,2S)-N-dodecyl-N,N-dimethylpseudoephedrinium bromide 
• 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

Stereospecific Conversion of N,N-Dimethylamphetamine into N-Methylpseudoephedrine

The pro-R hydrogen of (+)-N,N-dimethylamphetamine chromium tricarbonyl can be stereospecifically substituted via sequential treatment with BunLi and an electrophile, with retention of configuration to give for example 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.

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.

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.

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.

Synthesis of syn- and anti-1,2-amino alcohols by regioselective ring opening reactions of cis-3-aminooxetanes

N-t-Butyloxycarbonyl (Boc) substituted cis-2-phenyl-3-aminooxetanes 3 undergo a ring expansion to oxazolidinones 5 upon treatment with trifluoroacetic acid. The reaction occurs at the C(2) position under inversion of configuration. Alternatively, 3-aminooxetanes can be ring-opened at the less substituted C(4) position with retention of the relative configuration between C(2) and C(3) as exemplified by the synthesis of (+)-pseudoephedrine (2). The cis3-aminooxetanes serve as precursors for either syn- or anti-1,2-amino alcohols.

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.