42407-58-9

Upstream product

• 321-97-1 (1R,2R)-pseudoephedrine 
• 645-45-4 hydrocinnamic acid chloride 
• 299-42-3 ephedrine 
• 90-82-4 pseudoephedrine 

Downstream Products

• 175979-80-3 <1S(2S),2S>-N-(2-hydroxy-1-methyl-2-phenylethyl)-4-hydroxy-N,4-dimethyl-2-(phenylmethyl)pentanamide 
• 173054-08-5 <1S(R),2S>-N-(2-hydroxy-1-methyl-2-phenylethyl)-4-(tert-butyldimethylsilyloxy)-N-methyl-2-(phenylmethyl)butanamide 
• 175979-71-2 (2S,4R)-2-Benzyl-5-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 175979-77-8 (2S,4S)-2-Benzyl-4-hydroxy-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 122-97-4 3-Phenyl-1-propanol 
• 175979-72-3 (2S,4R)-2-Benzyl-5-benzyloxy-4-hydroxy-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 176198-64-4 (R)-2-Benzyl-4-hydroxy-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-butyramide 

Relevant academic research and scientific papers

Michael Reactions of Pseudoephedrine Amide Enolates: Effect of LiCl on Syn/Anti Selectivity

The stereochemical outcome of the asymmetric Michael reaction of pseudoephedrine amide enolates changes dramatically in the presence of LiCl. Reaction of the enolate in the absence of LiCl results in formation of the anti Michael adduct with high selectiv

Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones

The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.

Synthesis of compounds with predetermined chirality

A method for synthesizing enantiomerically enriched chemical intermediates with predetermined chirality is described. The method comprises formation of a pseudoephedrine amide, followed by stereoselective alkylation at the alpha carbon. The chiral auxiliary can then be cleaved off, affording chiral end products useful for further transformations. The enantiomeric enrichment of the chiral end products may exceed 98%, and the chiral auxiliary can be recovered. Novel amides of pseudoephedrine used in this method are also disclosed.