220037-58-1

Basic information

• Product Name: (S)-Pyrrolidine-2-carboxylic acid (3,5-dimethyl-phenyl)-amide
• Synonyms: (S)-Pyrrolidine-2-carboxylic acid (3,5-dimethyl-phenyl)-amide
• CAS NO: 220037-58-1
• Molecular Weight: 218.299
• Mol File: 220037-58-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (S)-Pyrrolidine-2-carboxylic acid (3,5-dimethyl-phenyl)-amide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Pyrrolidine-2-carboxylic acid (3,5-dimethyl-phenyl)-amide(220037-58-1)
• EPA Substance Registry System: (S)-Pyrrolidine-2-carboxylic acid (3,5-dimethyl-phenyl)-amide(220037-58-1)

Safety Data

• Hazardous Substances Data: 220037-58-1(Hazardous Substances Data)

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 108-69-0 3,5-dimethylaminoaniline 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 150258-54-1 (S)-2-(3,5-Dimethyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 137496-70-9 (S)-tert-butyl 2-((3,5-dimethylphenyl)carbamoyl)pyrrolidine-1-carboxylate 

Downstream Products

• 1361321-96-1 (S)-1-(4-methoxy-benzenesulfonyl)-pyrrolidine-2-carboxylicacid (3,5-dimethyl-phenyl)-amide 
• 1092577-93-9 C₁₇H₂₆N₂O₂S 
• 1092577-91-7 C₁₇H₂₆N₂O₂S 
• 220665-59-8 (3,5-Dimethyl-phenyl)-(S)-1-pyrrolidin-2-ylmethyl-amine 

Relevant articles and documents

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

A highly enantioselective organocatalytic method for reduction of aromatic N-alkyl ketimines

A study has demonstrated the development of a highly enantioselective catalytic method for the reduction of aromatic N-alkyl ketimines by trichlorosilane under mild conditions using the newly designed Lewis base organocatalyst that incorporates C- and S-chirality. The S-chiral sulfinamide group in these catalysts plays a crucial role similar to the carboxamide groups as Lewis base for the activation of HSiCl3, and also serves as a source of chirality that the carboxamide group lacks for the asymmetric induction. The results of the study showed that excellent enantioselectivities of up to 99.6% ee and high yields were obtained for a wide range of substrates. Further works is also in progress to clarify the mechanism of the transformation and explore the full application scope of the present catalyst system.

On-bead combinatorial approach to the design of chiral stationary phases for HPLC

A library of 36 L-amino acid anilides, which are potential selectors for chiral HPLC, was synthesized in solution and attached to functionalized macroporous polymer beads. The best selector from the library was identified by a deconvolution process using