51018-28-1

Basic information

• Product Name: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE
• Synonyms: (+)-1S,2S-METHYLPSEUDOEPHEDRINE;(1S,2S)-(+)-N-METHYLEPHEDRINE;(+)-1S,2S-N-METHYLPSEUDOEPHEDRINE;(1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE;(1S,2S)-(+)-N-METHYL-PSI-EPHEDRINE;METHYLPSEUDOEPHEDRINE;METHYLPSEUDOEPHEDRINE, (+)-1S,2S-;METHYLPSEUDOEPHEDRINE, (+)-1S,2S-N-
• CAS NO: 51018-28-1
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26
• EINECS: 209-022-7
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 51018-28-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 29-31 °C(lit.)
• Boiling Point: 145 °C24 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.0020 (rough estimate)
• Vapor Pressure: 0.0108mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.88±0.20(Predicted)
• CAS DataBase Reference: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE(51018-28-1)
• EPA Substance Registry System: (1S,2S)-(+)-N-METHYLPSEUDOEPHEDRINE(51018-28-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 1544
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 51018-28-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

N-Methylpseudoephedrine is a N-methylated analogue of the non-selective adrenergic agonist Pseudoephedrine (P839350). N-Methylpseudoephedrine is an alkaloid from Ephedra species widely used in Chinese medicine.

InChI:InChI=1/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11+/m0/s1

Upstream product

• 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 
• 50-00-0 formaldehyd 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 130459-53-9 (1R,2S)-2-(tert-butoxycarbonyl(methyl)amino)-1-phenyl-1-propanol 
• 90-82-4 pseudoephedrine 
• 74-88-4 methyl iodide 
• 16251-47-1 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-one 
• 66574-19-4 (4S,5S)-3,4-dimethyl-5-phenyl-1,3-oxazolidine 
• 35026-77-8 (S)-2-(dimethylamino)propiophenone 

Downstream Products

• 479350-68-0 (S,S)-N-methylpseudoephedrine 2-bromo-4-phenylbutanoate 
• 116588-21-7 (1S,2S)-2-(Dimethylamino)-1-phenyl-1-(phenylthio)propane 
• 47497-54-1 (1S,2S)-N-Methylpseudothioephedrine disulfide 
• 2226-22-4 (1S,2S)-2-(Dimethylamino)-1-phenyl-1-(acetylthio)propane 
• 158837-63-9 (1S,2S)-1-Phenyl-1-phthalimido-2-(dimethylamino)propane 
• 1078720-31-6 (1S,2S)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N,N-dimethyl-hexadecan-1-ammonium bromide 
• 74059-55-5 (1S,2S)-N-methyl-ψ-ephedrine propionate 
• 1041013-28-8 (1S,2S)-2-(dimethylamino)-1-phenylpropyl 3-[(4-fluorobenzoyl)amino]-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate 
• 1017295-11-2 (R(p))-1,2-ferrocenediyl(BMe(OMe))(SnMe₂Cl) 

Relevant articles and documents

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.

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.

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.