826994-64-3

Basic information

• Product Name: 1-Pyrrolidinepropanoic acid, 2-[[(4-methylphenyl)sulfonyl]methylene]-, ethyl ester, (2E)-
• CAS NO: 826994-64-3
• Molecular Formula: C17H23NO4S
• Molecular Weight: 337.44
• Mol File: 826994-64-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinepropanoic acid, 2-[[(4-methylphenyl)sulfonyl]methylene]-, ethyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinepropanoic acid, 2-[[(4-methylphenyl)sulfonyl]methylene]-, ethyl ester, (2E)-(826994-64-3)
• EPA Substance Registry System: 1-Pyrrolidinepropanoic acid, 2-[[(4-methylphenyl)sulfonyl]methylene]-, ethyl ester, (2E)-(826994-64-3)

Safety Data

• Hazardous Substances Data: 826994-64-3(Hazardous Substances Data)

Upstream product

• 5366-49-4 4-toluenesulfonylacetone 
• 61930-87-8 1-(2-oxopyrrolidine)propanoic acid ethyl ester 
• 74991-93-8 ethyl 3-(2-thioxopyrrolidin-1-yl)propanoate 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 826994-66-5 8-[(4-methylphenyl)sulfonyl]-2,3,5,6-tetrahydroindolizin-7(1H)-one 
• 826994-65-4 1,2,3,5,6,7-hexahydroindolizin-8-yl 4-methylphenyl sulfone 
• 826994-82-5 3-((2E)-2-{[(4-methylphenyl)sulfonyl]methylene}pyrrolidin-1-yl)propan-1-ol 

Relevant articles and documents

Preparation and reductive transformations of vinylogous sulfonamides (β-sulfonyl enamines), and application to the synthesis of indolizidines

Condensation between the methiodide salts of 1-alkylpyrrolidine-2-thiones and ethyl [(4-methylphenyl)sulfonyl]acetate or 1-[(4-methylphenyl)sulfonyl]propan-2-one afforded several 2-{[(4-methylphenyl)sulfonyl]methylene}pyrrolidines in good yield. These β-sulfonyl enamines are sufficiently nucleophilic for cyclisation with internal electrophiles to give sulfone-substituted indolizines, potentially useful scaffolds for alkaloid synthesis. The carbon-carbon double bond in vinylogous sulfonamides was reduced stereoselectively either by catalytic hydrogenation or by treatment with sodium borohydride to yield β-sulfonyl amines. The sulfone group in β-acyl-β-sulfonyl enamines could be removed by hydrogenolysis with sodium amalgam in THF-methanol to give enaminones.