61347-76-0

Basic information

• Product Name: NH-benzyl-(1R,2S)-norephedrine
• Synonyms: NH-benzyl-(1R,2S)-norephedrine
• CAS NO: 61347-76-0
• Molecular Weight: 241.333
• Mol File: 61347-76-0.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: NH-benzyl-(1R,2S)-norephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: NH-benzyl-(1R,2S)-norephedrine(61347-76-0)
• EPA Substance Registry System: NH-benzyl-(1R,2S)-norephedrine(61347-76-0)

Safety Data

• Hazardous Substances Data: 61347-76-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 100-46-9 benzylamine 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 67-56-1 methanol 
• 70735-98-7 (+/-)-4r-methyl-2ξ,5t-diphenyl-oxazolidine 
• 52597-17-8 2-(N-benzylamino)-1-phenyl-1-propanone 
• 64-17-5 ethanol 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 532-28-5 (RS)-mandelonitrile 
• 698352-11-3 2-(N-benzyl-N-tert-butoxycarbonylamino)-1-phenyl-1-propanone 
• 698351-56-3 benzyl-(2-hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 

Downstream Products

• 117693-80-8 (+/-)-3-benzyl-4r-methyl-2ξ,5t-diphenyl-oxazolidine 
• 190724-36-8 Benzyl-((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-carbamic acid ethyl ester 
• 613688-62-3 [benzyl[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]amino]acetonitrile 
• 492-41-1 (1R,2S)-norephedrine 
• 190724-40-4 (4S,5S)-3-Benzyl-4-methyl-5-phenyl-oxazolidin-2-one 
• 61347-73-7 (1S,2S)-2-(benzylamino)-1-phenyl-1-propanol 
• 198906-19-3 (1'R/S,2R,4S,5R)-2-[(1'-Cyano-1'-phenyl)methoxy]-3-benzyl-4-methyl-5-phenyl-1,3,2-oxazaphospholidin-2-one 
• 613688-74-7 (S)-2-[((2S,3S,4S)-1-Benzyl-4-methyl-3-phenyl-azetidine-2-carbonyl)-amino]-propionic acid methyl ester 

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.

β-Amino alcohols derived from (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine as catalysts in the asymmetric addition of diethylzinc to aldehydes

A family of N-alkylnorephedrine and N-alkylpseudonorephedrine derived ligands were prepared and applied in the asymmetric alkylation of benzaldehyde using diethylzinc. The absolute configuration of the addition product was directed primarily by the benzylic position of the Ephedra alkaloid, while the magnitude of the enantiomeric ratio was heavily influenced by the nitrogen substituent. However, sterically demanding substituents at the nitrogen position caused the enantioselectivity to be the same for the two diastereomeric systems. Among the ligands that were prepared, it was determined that the N-cyclooctylpseudonorephedrine derivative 7b yielded the highest enantiomeric ratios (87.5:12.5 to 91.0:9.0) when applied in the catalytic asymmetric addition of diethylzinc to aldehydes.

Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols

Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt 3BH or Li(S-Bu)3BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β- aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations.