48141-64-6

Usage

Uses

Used in Pharmaceutical Research:
[R-(R,S)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol is used as a precursor in the pharmaceutical industry for the synthesis of various organic compounds. Its chiral nature makes it particularly valuable for asymmetric synthesis, which is crucial in the development of enantiomerically pure drugs with desired biological activities.
Used in Chemical Research:
In the field of chemical research, [R-(R,S)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol serves as a key intermediate in the synthesis of complex organic molecules. Its unique structure allows for further functionalization and modification, enabling the creation of novel compounds with potential applications in various industries.
Used in Synthesis of Chiral Compounds:
Due to its chiral nature, [R-(R,S)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol is used as a building block in the synthesis of chiral compounds. These chiral compounds have applications in various fields, including pharmaceuticals, agrochemicals, and materials science, where they can exhibit different biological activities based on their stereochemistry.
Used in Drug Delivery Systems:
[R-(R,S)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol can be employed in the development of drug delivery systems, where its chiral properties may contribute to the selective targeting of specific biological receptors or the enhancement of drug solubility and bioavailability.
Used in Analytical Chemistry:
[R-(R,S)]-alpha-[1-(ethylmethylamino)ethyl]benzyl alcohol's unique structure and chiral properties make it a valuable tool in analytical chemistry for the development of chiral stationary phases for chromatography, which are essential for the separation and analysis of enantiomers in various samples.

Upstream product

• 64-67-5 diethyl sulfate 
• 299-42-3 ephedrine 
• 2272-83-5 (1R,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid 
• 75-05-8 acetonitrile 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 50-00-0 formaldehyd 
• 37025-57-3 N-ethylnorephedrine 
• 258827-42-8 (4S,5R)-2,3,4-Trimethyl-5-phenyl-oxazolidine 
• 74-96-4 ethyl bromide 

Downstream Products

• 145388-31-4 (2S)-2<2(Ethyl-methyl-amino)propyl>-N,N-dimethylphenylacetamid 
• 139528-43-1 (1R,2S)-α-<1-(ethylmethylamino)ethyl>benzylamine 
• 139528-44-2 2-[(1R,2S)-2-(Ethyl-methyl-amino)-1-phenyl-propyl]-isoindole-1,3-dione 
• 145388-32-5 (2S)-1<2-(2-Dimethylaminoethyl)phenyl>-N-ethyl-N-methyl-2-propanamin 
• 139528-45-3 (1R,2S)-α-<1-(ethylmethylamino)ethyl>-N-cyclohexylbenzylamine 

Relevant academic research and scientific papers

Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides

Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species – plausibly zincates – which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100 %. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium β-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(–)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100 % yield.

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.

Nitriles under palladium-catalyzed hydrogenation conditions as substitutes for aldehydes in the reaction with 1,2-amino alcohols: Formation of 1,3-oxazolidines and reductive N-alkylation

At room temperature, the presence of hydrogen and catalytic amounts of Pd/C induced the formation of 1,3-oxazolidines from nitriles and 1,2-amino alcohols. The subsequent reductive cleavage of the NC-O bond of these heterocycles occurred under the same conditions. Thus, this methodology provides a new one-pot N-alkylation of 19-amino alcohols using nitriles as reagents with yields up to 98%.

Reactions of (-)-Ephedrine, (+)-Norpseudoephedrine and Derivatives with N,N-Dimethylacetamid-dimethylacetal and N,N-Dimethylformamid-dimethylacetal

The reactivity of (-)-ephedrine (2) and (+)-norpseudoephedrine (3) towards the amid-acetals 1 a/b has been studied.Both 2 and 3 were acetylated resp. formylated at first at the amino group.Nevertheless, derivatives of 2 and 3 possessing a trisubstituted amino group react with 1 a in a sigmatropic rearrangement to ortho substituted dimethylcarbamoylmethyl derivatives.By subsequent reduction with lithiumaluminiumhydride the aromatic compounds 8, 13, and 18 with two aminoethyl groups are easily available.In contrast to these results 1 b did not furnish any rearrangement products. Keywords. (-)-Ephedrine; (+)-Norpseudoephedrine; N,N-Dimethylacetamid-dimethylacetal; N,N-Dimethylformamid-dimethylacetal; Sympathomimetic effects; Sigmatropic rearrangements.