223268-30-2

Basic information

• Product Name: 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol
• Synonyms: 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol
• CAS NO: 223268-30-2
• Molecular Weight: 241.333
• Mol File: 223268-30-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol(223268-30-2)
• EPA Substance Registry System: 2-<(1R)-1-(<(1'R)-1'-phenylethyl>amino)ethyl>phenol(223268-30-2)

Safety Data

• Hazardous Substances Data: 223268-30-2(Hazardous Substances Data)

Upstream product

• 95255-51-9 (-)-2-{1-{[(1R)-1-phenylethyl]imino}ethyl}phenol 
• 917-54-4 methyllithium 
• 3266-80-6 (R,E)-2-(((1-phenylethyl)imino)methyl)phenol 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 123983-05-1 2?[(1R)?1-aminoethyl]phenol 
• 223269-04-3 (4R)-4-methyl-3-<(1'R)-1'-phenylethyl>-3,4-dihydro-2H-1,3-benzoxazine 

Relevant articles and documents

Asymmetric Syntheses of 2-(1-Aminoethyl)phenols

Three different routes were probed for the synthesis of enantiomerically enriched 2-(1-aminoethyl)phenols and their methyl ethers. The first route centers on diastereoselective nucleophile addition to chiral imines. The second route has as key steps the enantioselective reduction of a ketone followed by nucleophilic substitution, and the third route involves a diastereoselective imine reduction. The efficiency of the approach depends on the substrate substitution pattern. All three methods work well for the parent compound 2-(1-aminoethyl)phenol (1) but the third route is the most efficient, providing the compound with >96% enantiomer excess in three steps with an overall yield of 71%. Conversely, for the ortho-methyl analogue 2, the first method is best. For the t-Bu-substituted analogue 3, only moderate enantiomeric enrichment was achieved.

Ready N-alkylation of enantiopure aminophenols: Synthesis of tertiary aminophenols

A regioselective indirect alkylation of aminophenols to enantiopure tertiary aminophenols, which are useful chiral ligands for metal-catalysed asymmetric reactions, is reported. This very simple synthetic methodology, through reduction or alkylation of an intermediate benzoxazine, was performed in mild conditions, suitable for the conservation of the configuration of the stereogenic centres. Some crystalline aminophenols show the phenomenon of 'crystallization-induced asymmetric transformation'.

Synthesis of enantiopure o-hydroxybenzylamines by stereoselective reduction of 2-imidoylphenols: Application in the catalytic enantioselective addition of diethylzinc to aldehydes

Enantiopure o-hydroxybenzylamines 2a-i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a-i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a-i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a-f.