352530-53-1

Usage

InChI:InChI=1/C10H15NO.C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9;1-8(10(11)12)7-9-5-3-2-4-6-9/h3-8,10-12H,1-2H3;2-6,8H,7H2,1H3,(H2,11,12)/t8-,10+;8-/m10/s1

Upstream product

• 14980-86-0 N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-phenylpropanamide 
• 74-88-4 methyl iodide 
• 299-42-3 ephedrine 
• 14367-67-0 2-methyl-3-phenylpropionic acid 
• 1009-67-2 2-methyl-3-phenylpropionic acid 
• 100-39-0 benzyl bromide 
• 192060-67-6 (1R,2R)-(-)-pseudoephedrinepropionamide 
• 645-45-4 hydrocinnamic acid chloride 
• 90-82-4 pseudoephedrine 
• 108-90-7 chlorobenzene 
• 159213-03-3 N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide 

Downstream Products

• 154920-05-5 (2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol 

Relevant academic research and scientific papers

A convenient, NMR-based method for the analysis of diastereomeric mixtures of pseudoephedrine amides

(Chemical Equation Presented) Amides of pseudoephedrine and ephedrine are shown to undergo highly stereospecific, invertive cyclization to form 4,5-dihydro-3,4-dimethyl-5-phenyl-1,3-oxazolium triflate derivatives in the presence of triflic anhydride-pyrid

Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation

Pseudoephedrine-derived dianionic Myers enolates were generated using sodium diisopropylamide (NaDA) in THF solution. The reactivities and selectivities of the disodium salts largely mirror those of the dilithium salts but without the requisite large exce

Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides

Figure Presented. Enantiomerically enriched potassium β- trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling react

Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase

A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from the resin in high enantiomeric excess and moderate to good overall yield. The parallel, asymmetric solid-phase synthesis of a small library of chiral ketones and alcohols has been carried out to illustrate the utility of the approach. Finally, the pseudoephedrine resin can be conveniently recycled and utilized with no significant loss in the yield or enantiomeric excess of the products.

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

(Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.

Syntheses of the C-1 alkyl side chains of Zaragozic acids A and C

Asymmetric syntheses of the C-1 alkyl side chains of Zaragozic acids A and C from a common chiral precursor 4 are reported. The stereoselective reduction of unsaturated ketones 8 and 10 is the key step of both syntheses.

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.

Asymmetric synthesis of 1,3-dialkyl-substituted carbon chains of any stereochemical configuration by an iterable process

A highly practical, iterable method for the preparation of 1,3,5,n(odd)-polyalkyl-substituted carbon chains based upon the asymmetric alkylation of pseudoephedrine amide enolates is described.

Studies towards the synthesis of the zaragozic acids: Synthesis of the bicyclic acetal core of zaragozic acid C.

The bicyclic core 6 of zaragozic acid C (7) was prepared by the epoxide cyclisation reaction 21 → 22 → 15. Acetal 15 was also obtained by acid-promoted rearrangement of the isomeric acetal 19.