81330-01-0

Basic information

• Product Name: (2R,5S)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine
• Synonyms: Pyrrolidine, 2,5-dimethyl-1-((4-methylphenyl)sulfonyl)-, cis-
• CAS NO: 81330-01-0
• Molecular Formula: C₁₃H₁₉NO₂S
• Molecular Weight: 253.3605
• Mol File: 81330-01-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 364.5°C at 760 mmHg
• Flash Point: 174.2°C
• Density: 1.134g/cm³
• Vapor Pressure: 1.68E-05mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: (2R,5S)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine(81330-01-0)
• EPA Substance Registry System: (2R,5S)-2,5-dimethyl-1-[(4-methylphenyl)sulfonyl]pyrrolidine(81330-01-0)

Safety Data

• Hazardous Substances Data: 81330-01-0(Hazardous Substances Data)

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 81329-98-8 N-(hexan-2-yl)-4-methylbenzenesulfonamide 
• 110-62-3 pentanal 
• 592-45-0 1,4-hexadiene 
• 18522-92-4 sodium p-toluenesulfonamide 
• 123993-66-8 (2S*,5S*)-2-acetoxy-5-(tosylamido)-3-hexene 
• 123993-70-4 (E)-(R*,S*)-5-(p-toluenesulfonamido)-3-hexen-2-yl acetate 
• 123993-77-1 (E)-(R*,R*)-5-(p-Toluenesulfonamido)-3-hexen-2-ol 
• 123993-74-8 (E)-(R*,S*)-2-(p-toluenesulfonamido)-3-hexen-5-ol 
• 123993-85-1 N-((1R,4R)-4-Hydroxy-1-methyl-pentyl)-4-methyl-benzenesulfonamide 
• 123993-81-7 (R*,S*)-2-(p-toluenesulfonamido)hexan-5-ol 
• 124095-79-0 (E)-(R*,R*)-5-chloro-3-hexen-2-yl acetate 
• 124095-80-3 (E)-(R*,S*)-5-chloro-3-hexen-2-yl acetate 
• 898832-97-8 N-(1-methylpent-4-en-1-yl)(4-methylphenyl)sulfonamide 

Relevant articles and documents

Triiodide-Mediated δ-Amination of Secondary C?H Bonds

The Cδ?H amination of unactivated, secondary C?H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3?)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3?, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.

Gold versus silver-catalyzed intermolecular hydroaminations of alkenes and dienes

Comparative studies about the hydroamination of unactivated alkenes and dienes catalyzed by either cationic gold(I) triphenyl phosphite complexes or silver salts were performed using sulfonamides, anilines and carbamates as nucleophiles. Gold-catalyzed reactions generally, need lower loadings than those carried out with silver salts. Simple alkenes react only with sulfonamides and weak aromatic amines such as p-nitroaniline, whereas for conjugated dienes carbamates can also be used. Carbon-carbon double bond isomerization is observed only with gold similarly to when triflic acid was used, affording mixtures of regioisomeric products in the same cases. Silver-catalyzed hydroaminations failed with terminal alkenes, except with styrenes. Conjugate dienes can be hydroaminated either at 85 °C in toluene or at room temperature in dichloromethane. Non-conjugated 1,4- and 1,5-dienes suffer double hydroamination leading to saturated N-tosylated heterocyclic amines The catalytic cycle for the silver(I)-catalyzed hydroamination process has been computationally analyzed, resembling gold(I)-catalyzed processes, although with some significant differences. Copyright

Gold(I)-catalyzed intra- and intermolecular hydroamination of unactivated olefins

Ph3PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides. Copyright