145774-77-2

Basic information

• Product Name: methyl N-(1-phenylethyl)-α-iminoacetate
• Synonyms: methyl N-(1-phenylethyl)-α-iminoacetate
• CAS NO: 145774-77-2
• Molecular Weight: 191.23
• Mol File: 145774-77-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl N-(1-phenylethyl)-α-iminoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(1-phenylethyl)-α-iminoacetate(145774-77-2)
• EPA Substance Registry System: methyl N-(1-phenylethyl)-α-iminoacetate(145774-77-2)

Safety Data

• Hazardous Substances Data: 145774-77-2(Hazardous Substances Data)

Upstream product

• 109745-70-2 methyl glyoxylate methyl hemi-acetal 
• 618-36-0 rac-methylbenzylamine 
• 922-68-9 Methyl glyoxylate 

Downstream Products

• 51731-17-0 trans-4-methoxy-3-buten-2-one 
• 130135-88-5 exo-2-aza-2-(1-phenylethyl)-3-methoxycarbonyl-<2,2,1>-bicyclohept-5-ene 
• 130135-88-5 endo-2-aza-2-(1-phenylethyl)-3-methoxycarbonyl-<2,2,1>-bicyclohept-5-ene 

Relevant articles and documents

A new method for the preparation of functionalized unnatural α-H-α-amino acid derivatives

A new method for the preparation of α-H-α-amino acids is reported based on the α-alkylation of iminoacetic acid esters or amides. These imines are readily available by the reaction of glyoxylic acid esters with branched primary amines. The subsequent reaction with methanolic ammonia gave the corresponding iminoacetic acid amides. α-Alkylation of these imines with various electrophiles under basic conditions, followed by an acidic hydrolysis, gave α-amino acids, esters, or amides in up to 93% yield. α-Alkylation under chiral PTC conditions resulted in mono-alkylated amino acids with 90% ee.

SYNTHESE DE DERIVES DE L'ACIDE PIPECOLIQUE PAR REACTION D'AZA-DIELS-ALDER : CYCLOADDITIONS ACTIVEES PAR L'IODURE DE ZINC ENTRE LA 1-(PHENYL)-ETHYLIMINE DU GLYOXYLATE DE METHYLE ET LES DIENES RICHES EN ELECTRONS

The methyl N-(1-phenylethyl)-α-iminoacetate undergoes zinc iodide activated aza-Diels-Alder cycloaddition reactions with electron rich conjugated dienes.Cyclic α-amino-acids are formed in good yields, with complete regioselectivity, but the extent of asymmetric induction by the chiral phenethyl group on the nitrogen is low. KEY WORDS: aza-Diels-Alder reactions; heterocyclic α-amino-acids

Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate

The Diels-Alder reaction between cyclopentadiene and the chiral 1-phenyl-ethyl imine of methyl glyoxylate takes place very easily by activation with trifluoroacetic acid and boron trifluoride etherate to provide diastereoselectively (total face selectivit