57286-93-8

Basic information

• Product Name: (1R)-1-(4-Methoxyphenyl)-2-(methylamino)ethanol
• Synonyms: (1R)-1-(4-Methoxyphenyl)-2-(methylamino)ethanol;(R)-4-Methoxy-α-[(methylamino)methyl]benzenemethanol;[R,(-)]-p-Methoxy-α-[(methylamino)methyl]benzyl alcohol;Longimammine
• CAS NO: 57286-93-8
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• Mol File: 57286-93-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 315.4±32.0 °C(Predicted)
• Appearance: /
• Density: 1.067±0.06 g/cm3(Predicted)
• PKA: 14.09±0.20(Predicted)
• CAS DataBase Reference: (1R)-1-(4-Methoxyphenyl)-2-(methylamino)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1-(4-Methoxyphenyl)-2-(methylamino)ethanol(57286-93-8)
• EPA Substance Registry System: (1R)-1-(4-Methoxyphenyl)-2-(methylamino)ethanol(57286-93-8)

Safety Data

• Hazardous Substances Data: 57286-93-8(Hazardous Substances Data)

Usage

Description

This alkaloid, isolated from Dolicothele longimamma, differs from the accompanying bases in not having an isoquinoline structure. Instead, it belongs to the phenethylamine class of alkaloids. It is extracted from the EtOH fraction as the crystalline hydrochloride which forms colourless needles with m.p. 144- 6°C. This salt is optically active with a specific rotation of [α]25D - 76° and gives an ultraviolet spectrum in EtOH having absorption maxima at 225, 274 and 281 nm. The free base, prepared from the hydrochloride by standard chemical methods cannot be obtained in a crystalline form.

References

Ranieri, McLaughlin,J. Org. Chem., 41, 319 (1976)

Upstream product

• 117712-19-3 1-(4-methoxy-phenyl)-2-methylamino-ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 97070-73-0 (R)-(+)-α-Hydroxy-4-methoxybenzeneacetonitrile 
• 142429-14-9 (R)-(+)-<(2-methoxy-iso-propyl)oxy>-4-methoxybenzeneacetonitrile 
• 74-89-5 methylamine 
• 131043-85-1 (4R,5R)-5-(4-Methoxy-phenyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazole 
• 104383-29-1 methyl (S)-α-hydroxy-(4-methoxyphenyl)acetate 
• 87920-02-3 4-methoxy-L-mandelic acid-methylamide 
• 186581-53-3 diazomethane 
• 532-80-9 (+)-Synephrine 

Relevant articles and documents

Method for synthesizing chiral alpha-amino alcohol compound

The invention discloses a method for synthesizing a chiral alpha-amino alcohol compound. The method comprises the following steps: sequentially adding an iron catalyst, a ligand, ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the obtained mixture, and carrying out column chromatography separation on the obtained product to obtain a product, namely chiral alpha-amino alcohol. According to the invention, the most high-yield iron catalyst in earth crust is used, and cheap silane (PMHS, 500 g/298 yuan) is adopted as a reducing agent, so the asymmetric reduction reaction of alpha-amino ketone can be efficiently achieved under mild conditions so as to obtain the high-yield optically-active chiral alpha-amino alcohol compound; and moreover, through the creative labor of the inventor, reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99%.

The Asymmetric Aldol Reaction of Tosylmethyl Isocyanide and Aldehydes Catalyzed by Chiral Silver(I) Complexes

The asymmetric aldol reaction of tosylmethyl isocyanide and aldehydes in the presence of 1 mol percent of chiral silver(I) catalysts gave optically active 5-alkyl-4-tosyl-2-oxazolines (up to 86percent ee), which were converted to optically active α-alkyl-β-(N-methylamino)ethanols by LiAlH4 reduction.