180196-08-1

Basic information

• Product Name: (S)-[(S)-1-((R)-1-Phenyl-ethyl)-aziridin-2-yl]-o-tolyl-methanol
• Synonyms: (S)-[(S)-1-((R)-1-Phenyl-ethyl)-aziridin-2-yl]-o-tolyl-methanol
• CAS NO: 180196-08-1
• Molecular Weight: 267.371
• Mol File: 180196-08-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-[(S)-1-((R)-1-Phenyl-ethyl)-aziridin-2-yl]-o-tolyl-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-[(S)-1-((R)-1-Phenyl-ethyl)-aziridin-2-yl]-o-tolyl-methanol(180196-08-1)
• EPA Substance Registry System: (S)-[(S)-1-((R)-1-Phenyl-ethyl)-aziridin-2-yl]-o-tolyl-methanol(180196-08-1)

Safety Data

• Hazardous Substances Data: 180196-08-1(Hazardous Substances Data)

Upstream product

• 173143-73-2 N-<(R)-(+)-α-methylbenzyl>aziridine-2(S)-methanol 
• 95-46-5 2-methylphenyl bromide 
• 180196-03-6 (2S)-1-[(1R)-1-phenylethyl]aziridine-2-carbaldehyde 

Relevant articles and documents

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.