16257-57-1

Basic information

• Product Name: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE
• Synonyms: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE;(2S,4R)-Methyl 4-hydro×y-1-tosylpyrrolidine-2-carbo×ylate;Methyl 4-hydroxy-1-tosylpyrrolidine-2-carboxylate;XUMMBVXGIOJOPC-PWSUYJOCSA-N
• CAS NO: 16257-57-1
• Molecular Formula: C₁₃H₁₇NO₅S
• Molecular Weight: 299.34
• Mol File: 16257-57-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 97-99°C
• Boiling Point: 455.3 °C at 760 mmHg
• Flash Point: 229.1 °C
• Appearance: /
• Density: 1.373 g/cm³
• Vapor Pressure: 4.43E-09mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C
• PKA: 13.88±0.40(Predicted)
• CAS DataBase Reference: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE(16257-57-1)
• EPA Substance Registry System: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE(16257-57-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16257-57-1(Hazardous Substances Data)

Usage

General Description

Methyl 4-hydroxy-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate is a chemical compound with the molecular formula C15H19NO5S. It is a white to off-white solid with a molecular weight of 325.4 g/mol. METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE is a member of the pyrrolidinecarboxylate family and contains a sulfonyl and methylphenyl group. It is commonly used as a pharmaceutical intermediate in the synthesis of various drugs. Its versatile properties and reactivity make it a valuable building block in organic synthesis. Additionally, it has emerged as a potential target for medicinal chemistry research due to its pharmacological potential and therapeutic applications.

InChI:InChI=1/C13H17NO5S/c1-9-3-5-11(6-4-9)20(17,18)14-8-10(15)7-12(14)13(16)19-2/h3-6,10,12,15H,7-8H2,1-2H3/t10-,12-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 51-35-4 4R-4-hydroxyproline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 186581-53-3 diazomethane 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 67-56-1 methanol 

Downstream Products

• 16257-73-1 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 
• 261157-01-1 methyl N-toluenesulfonyl-O-t-butyldimethylsilyl-4-hydroxyprolinate 
• 863396-17-2 (2S)-1-(4-methylphenylsulfonyl)-2-vinylpyrrolidin-4-one 
• 863396-16-1 (2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine 
• 863396-18-3 (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde 
• 261157-02-2 (2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine 
• 870246-63-2 (2R)-2-(but-3-en-1-yl)-1-(4-methylphenyl)sulfonyl-2-pyrrolidin-4-one 
• 870246-70-1 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde 
• 870246-66-5 (2R,4R)-2-(but-3-en-1-yl)-4-(t-butyldimethylsilanyloxy)-1-(4-methylphenyl)sulfonyl-pyrrolidine 
• 870246-65-4 3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol 
• 870246-68-7 (E)-(R)-2-Butyl-10-(toluene-4-sulfonyl)-10-aza-bicyclo[7.2.1]dodec-5-en-1-ol 
• 870246-69-8 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester 
• 870246-62-1 (R)-5-But-3-enyl-3-(1-butyl-pent-4-enyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol 
• 2650-35-3 (–)-(6S,10aR,10bS)-norsecurinine 

Relevant articles and documents

Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin

The Pt-catalyzed diboration of cyclic alkenes is extended to unsaturated heterocycles and bicyclic compounds and can be accomplished in a diastereoselective fashion. The optimal procedures, substrate scope, and diastereoselectivity were investigated, and examples employing both homogeneous and heterogeneous catalysis were examined. Lastly, application to the construction of the nucleoside analog (±)-aristeromycin was conducted.

Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

A series of novel sulfonyl pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed.

Formal synthesis of epibatidine

A straightforward formal synthesis of epibatidine has been established starting from trans-(2S,4R)-4-hydroxyproline.