154170-05-5

Basic information

• Product Name: (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol
• Synonyms: (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol
• CAS NO: 154170-05-5
• Molecular Weight: 255.36
• Mol File: 154170-05-5.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol(154170-05-5)
• EPA Substance Registry System: (1R,2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanol(154170-05-5)

Safety Data

• Hazardous Substances Data: 154170-05-5(Hazardous Substances Data)

Upstream product

• 635304-48-2 (2S)-1-phenyl-2-[((1R)-phenylethyl)amino]-1-propanone methanesulfonate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 98-86-2 acetophenone 
• 492-41-1 (1R,2S)-norephedrine 
• 100-58-3 phenylmagnesium bromide 
• 180196-03-6 (2S)-1-[(1R)-1-phenylethyl]aziridine-2-carbaldehyde 
• 173143-73-2 N-<(R)-(+)-α-methylbenzyl>aziridine-2(S)-methanol 
• 108-86-1 bromobenzene 
• 180323-00-6 (R)-phenyl{(S)-1-[(R)-1-phenylethyl]aziridin-2-yl}methanol 

Downstream Products

• 492-41-1 (1R,2S)-norephedrine 
• 1161754-77-3 (1R,2S,1'R)-(-)-2-(1'-phenylethylamino)-1-phenyl-1-propanol hydrochloride 

Relevant articles and documents

Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines

Enantiomerically pure N-alkylated β-amino alcohols 1a, 1a′, 1c, 1c′, 1d, 1d′, 1e and 1e′, with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (α- or β-) chiral environment. The antimicrobial activity of the synthesized β-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a′, 1c, 1c′, 1d, 1d′, 1e & 1e′ and amongst them 1d & 1d′ exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized β-amino alcohols 1a-e and 1a′-e′ have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d′ has shown maximum binding energy -7.38 kJ/mol.

PROCESS FOR PRODUCING OPTICALLY ACTIVE s-AMINO ALCOHOL

A process for easily producing an optically active β-amino alcohol useful as a pharmaceutical intermediate from an inexpensive, readily available starting material is provided. A readily available α-substituted ketone is reacted with an optically active amine to yield a diastereomer mixture of an optically active α-substituted aminoketone. One of the diastereomers is isolated optionally after the diastereomers are converted to salts with an acid. The optically active α-substituted aminoketone or a salt thereof thus isolated was stereoselectively reduced to yield an optically active β-substituted amino alcohol. The optically active β-substituted amino alcohol is subjected to hydrogenolysis to produce an optically active β-amino alcohol or a salt thereof.

An efficient synthesis of both enantiomers of Cathinone by regioselective reductive ring opening of substituted aziridines

Both enantiomers of Cathinone were prepared as HCl salts from N-(R)-α-methylbenzylaziridine-2(S)-carboxaldehyde 2c and its enantiomer N-(S)-α-methyl-benzylaziridine-2(R)-carboxaldehyde 3c in high yield. This process makes it possible to prepare other aromatic and heteroaromatic analogs of Cathinone efficiently.

Efficient synthesis of Ephedra alkaloid analogues using an enantiomerically pure N-[(R)-(+)-α-methylbenzyl]aziridine-2-carboxaldehyde

Efficient preparation of enantiomerically pure (2S)-aziridine-2-carboxaldehyde 9 and its 2(R) isomer and highly diastereoselective addition of organolithium reagents to the aldehyde 9 are described. The diastereoselectivity in additions of the lithium reagents seems to come from 'chelation-controlled' carbon-carbon bond formation and is influenced by the source of the organometallic compound, solvent, and the presence of a Li salt. The C(3)-N bond of the aziridine ring of the addition products was regioselectively reduced by catalytic hydrogenation in the presence of Pearlman's catalyst te provide enantiomerically pure 1,2-amino alcohols. The absolute stereochemistries of the amino alcohol 13a were assigned as (1S,2S) when the C-1 substituent was phenyl by comparison with those of commercially available norpseudoephedrine.