281664-25-3

Basic information

• Product Name: (R)-(+)-N-4-Methoxybenzyl-1-(4-methoxyphenyl)ethylamine
• Synonyms: (R)-(+)-N-4-Methoxybenzyl-1-(4-methoxyphenyl)ethylamine
• CAS NO: 281664-25-3
• Molecular Weight: 271.359
• Mol File: 281664-25-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (R)-(+)-N-4-Methoxybenzyl-1-(4-methoxyphenyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-N-4-Methoxybenzyl-1-(4-methoxyphenyl)ethylamine(281664-25-3)
• EPA Substance Registry System: (R)-(+)-N-4-Methoxybenzyl-1-(4-methoxyphenyl)ethylamine(281664-25-3)

Safety Data

• Hazardous Substances Data: 281664-25-3(Hazardous Substances Data)

Upstream product

• 6298-96-0 1(R)-(4-methoxyphenyl)-ethylamine 
• 2746-25-0 p-Methoxybenzyl bromide 
• 2393-23-9 4-methoxy-benzylamine 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 170222-00-1 (S)-1-(4-methoxyphenyl)ethyl-1,3,2-benzodioxaborole 
• 637-69-4 4-Methoxystyrene 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 281664-28-6 methyl (3S)-3-[(1R)-N-(4-methoxybenzyl)-1-(4-methoxyphenyl)ethylamino]-3-phenylpropanoate 
• 566930-77-6 4-Methoxy-N-[(S)-1-(4-methoxy-phenyl)-ethyl]-N-[(R)-1-(4-methoxy-phenyl)-ethyl]-benzamide 
• 566930-75-4 4-methoxy-N-(4-methoxy-benzyl)-N-[1-(4-methoxy-phenyl)-ethyl]-benzamide 

Relevant articles and documents

Protic additives or impurities promote imine reduction with pinacolborane

We report here that addition of stoichiometric amounts of alcohols or water to mixtures of imines and pinacolborane promote reduction reactions. The reactions of several imines were examined, revealing that alkyl imines were reduced, while aniline derived imines were not effectively reduced. The use of binol as an additive resulted in modest enantioinduction, however other chiral additives that were screened gave negligible enantioinduction. While the reactions described herein are not competitive in conversion with established imine reduction technologies, this work reveals that the presence of protic impurities must be considered as a promoter of side reactions in catalyzed imine hydroborations. Amines also promote imine reduction in certain cases, raising the possibility of a slow autocatalytic reaction. The ability of water or other protic impurities to promote the reduction of imines with pinacolborane represents an important identification of a potential source of background reaction in catalyzed reductions of imines.

Enantioselective Imine Reduction Catalyzed by Phosphenium Ions

The first use of phosphenium cations in asymmetric catalysis is reported. A diazaphosphenium triflate, prepared in two or three steps on a multigram scale from commercially available materials, catalyzes the hydroboration or hydrosilylation of cyclic imin

Synthesis of α-methyl kainic acid by stereospecific lithiation-dearomatizing cyclization of a chiral benzamide

Stereospecific lithiation of N-α-methylbenzyl benzamides gives configurationally stable tertiary benzyllithiums which undergo a stereospecific dearomatizing cyclization with >99% retention of stereochemistry. The products are partially saturated isoindolinones which carry a new fully-substituted stereogenic centre. A ten-step sequence converts one of these products to the α-methyl analogue of kainic acid.