159099-80-6

Basic information

• Product Name: (1S,2S)-2-(N-benzyl-N-methylamino)-1-phenyl-1-propanol
• Synonyms: (1S,2S)-2-(N-benzyl-N-methylamino)-1-phenyl-1-propanol
• CAS NO: 159099-80-6
• Molecular Weight: 255.36
• Mol File: 159099-80-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1S,2S)-2-(N-benzyl-N-methylamino)-1-phenyl-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-2-(N-benzyl-N-methylamino)-1-phenyl-1-propanol(159099-80-6)
• EPA Substance Registry System: (1S,2S)-2-(N-benzyl-N-methylamino)-1-phenyl-1-propanol(159099-80-6)

Safety Data

• Hazardous Substances Data: 159099-80-6(Hazardous Substances Data)

Upstream product

• 258827-44-0 (4S)-3,4r-dimethyl-2ξ,5t-diphenyl-oxazolidine 
• 85-44-9 phthalic anhydride 
• 109-72-8 n-butyllithium 
• 1068601-67-1 N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylmethacrylamide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 90-82-4 rac-pseudoephedrine 
• 16735-30-1 2-(N-benzyl-N-methylamino)-1-phenylpropan-1-one 
• 176538-73-1 Benzoic acid (1S,2R)-3-bromo-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-phenyl-propyl ester 
• 176538-75-3 Benzoic acid (1S,2S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-phenyl-propyl ester 
• 169557-51-1 Acetic acid (1S,2S)-2-benzoylamino-1-phenyl-propyl ester 
• 123537-84-8 (1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol 
• 134522-09-1 N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-benzamide; N-benzoyl-(+)-norpseudoephedrine 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 

Downstream Products

• 90-82-4 pseudoephedrine 

Relevant articles and documents

N-Pyridylmethylephedrine derivatives in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines

N-Pyridylmethyl-substituted Ephedra derivatives were synthesized by either direct alkylation or reductive alkylation of (1R,2S)-norephedrine, (1S,2S)-pseudo norephedrine, and (1R,2S)-ephedrine. These derivatives were then employed in asymmetric addition reactions with diethylzinc and aldehydes and diphenylphosphinoylimines. The use of the diastereomers from the Ephedra family allowed for a systematic evaluation of the contribution of the N-pyridylmethyl.

1,2-Aminothioethers Derived from Ephedrine and Pseudoephedrine: Heterobidentate Ligands for the Palladium-Catalysed Asymmetric Allylic Substitution Reaction

Heterobidentate sulfide-tertiary amine ligands incorporating 1,2-aminothioethers derived from ephedrine and pseudoephedrine have been prepared and used successfully in the palladium-catalysed asymmetric allylic substitution reaction, giving ees of up to 89 percent. The stereoelectronic effects operating in the reactions are discussed.

(1S,2S)-2-Amino-1-phenyl-1,3-propanediol, a spin off from chloramphenicol manufacture, as chiral synthon for (1S, 2S)-pseudoephedrine and (R)-phenylalaninol

(1S,2S)-2-Amino-1-phenyl-1,3-propanediol (3a), a discarded optically active material in one of the processes for the manufacture of chloramphenicol, has been transformed into (S,S)-pseudoephedrine (4) and (R)-phenylalaninol (5). The opposite selectivity of highly regioselective oxidative ring opening of the benzaldehyde acetal of (1S,2S)-2-phthalimido-1-phenyl-1,3-propanediol by NBS and highly regioselective ring opening of the cyclic sulphite of the same substrate by LiBr are the key steps in the transformations respectively.