42151-56-4

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Purification Methods

N-Methylephedrine has been recrystallised from Et2O, pet ether, of aqueous EtOH or aqueous MeOH and has been distilled under reduced pressure. [Smith J Chem Soc 2056 1927, Tanaka & Sugawa Yakugaku Zasshi (J Pharm Soc Japan) 72 1548 1952 (Chem Abstr 47 8682 1953), Takamatsu Yakugaku Zasshi (J Pharm Soc Japan) 76 1227 1956, Chem Abstr 51 4304 1957.] The hydrochloride has m 192-193o and [] D (c 5,H2O)[Prelog & Hüfliger Helv Chim Acta 33 2021 1950].20+30o [Beilstein 13 IV 1884.]

InChI:InChI=1/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/p+1/t9-,11-/m1/s1

Upstream product

• 90-82-4 pseudoephedrine 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 17279-39-9 (S)-N,N-dimethyl-α-benzylethylamine 
• 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 
• 130459-53-9 (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 15351-09-4 metamfepramone 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-55-0 1-phenyl-propan-1-one 
• 65528-82-7 (R)-2-(dimethylamino)propiophenone 
• 942-45-0 ((1R,2S)-2-chloro-1-methyl-2-phenyl-ethyl)-dimethyl-amine; hydrochloride 

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 
• 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

Plasmon resonance-enhanced circularly polarized luminescence of self-assembled meso-tetrakis(4-sulfonatophenyl)porphyrin-surfactant complexes in interaction with Ag nanoparticles

The chiroptical properties of an anionic meso-tetrakis(4-sulfonatophenyl) porphyrin (TPPS) complexed with cationic surfactants were enhanced by interaction with silver nanoparticles (AgNPs) in acidic solution. Improvement in chiroptical properties was rev

Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol

An iron(0) complex bearing a cyclopentadienone ligand catalyzed N-methylation and N-ethylation of aryl and aliphatic amines with methanol or ethanol in mild and basic conditions through a hydrogen autotransfer borrowing process is reported. A broad range of aromatic and aliphatic amines underwent mono- or dimethylation in high yields. DFT calculations suggest molecular hydrogen acts not only as a reducing agent but also as an additive to displace thermodynamic equilibria.

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.

Theoretical and Experimental Optimization of a New Amino Phosphite Ligand Library for Asymmetric Palladium-Catalyzed Allylic Substitution

A new library of modular amino phosphite ligands obtained in a few synthetic steps from enantiopure amino alcohols has been tested in asymmetric Pd-catalyzed allylic substitution. The modular ligand design is crucial to find highly selective catalysts for each substrate type using a wide range of C-, N-, and O-nucleophiles. A DFT study of the species responsible for the enantiocontrol was used to optimize the ligand structure. By selecting the ligand components, we were able to identify unprecedented catalytic systems that can create new chiral C-C, C-N, and C-O bonds in a variety of substrate types (hindered and unhindered) in high yields and enantioselectivities (ee values up to 99 %). Further studies on the Pd-π-allyl intermediates provided a deep understanding of the effect of ligand structure in the origin of enantioselectivity. Potential applications of the new Pd/amino phosphite catalysts were demonstrated by the practical synthesis of a range of chiral carbocycles by simple tandem reactions, with no loss of enantioselectivity.

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.