219783-11-6

Basic information

• Product Name: (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide
• Synonyms: (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide
• CAS NO: 219783-11-6
• Molecular Weight: 327.423
• Mol File: 219783-11-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide(219783-11-6)
• EPA Substance Registry System: (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide(219783-11-6)

Safety Data

• Hazardous Substances Data: 219783-11-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 159213-03-3 N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide 

Downstream Products

• 283151-89-3 [1R,2R]-(+)-1-hydroxy-2-methyl-1-phenyl-3-heptanone 
• 283151-79-1 [1S,2S,3R]-(+)-2-methyl-1-phenyl-1,3-butanediol 
• 180061-08-9 [1R,2S,3R]-(-)-2-methyl-1-phenyl-1,3-butanediol 
• 106471-21-0 (1S*,2r*,3R*)-2-Methyl-1,3-diphenylpropan-1,3-diol 
• 76549-05-8 methyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoate 
• 90-82-4 pseudoephedrine 
• 76549-04-7 (2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid 
• 283151-71-3 (2R,3R)-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one 
• 283151-88-2 [3R,4R]-(+)-4-hydroxy-3-methyl-4-phenyl-2-butanone 

Relevant articles and documents

Asymmetric aldol reactions using (S,S)-(+)-pseudoephedrine-based amides: Stereoselective synthesis of α-methyl-β-hydroxy acids, esters, ketones, and 1,3-syn and 1,3-anti diols

A very efficient method for performing stereoselective aldol reactions is reported. The reaction of (S,S)-(+)-pseudoephedrine-derived propionamide enolates with several aldehydes yielded exclusively one of the four possible diastereomers in good yields, although transmetalation of the firstly generated lithium enolate with a zirconium(II) salt, prior to the addition of the aldehyde, is necessary in order to achieve high syn selectivity. The so-formed syn-α-methyl-β-hydroxy amides were transformed into other valuable chiral nonracemic synthons such as α-methyl-β-hydroxyacids, esters, and ketones. Finally, a stereocontrolled reduction procedure starting from the so-obtained α-methyl-β-hydroxy ketones has been developed allowing the synthesis of either 1,3-syn- or 1,3-anti-α-methyl-1,3-diols in almost enantiopure form by choosing the appropriate reaction conditions.