128510-88-3

Basic information

• Product Name: (R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE
• Synonyms: (R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE;1-Pyrrolidinecarboxylicacid, 2-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-, 1,1-dimethylethyl ester,(2R)-
• CAS NO: 128510-88-3
• Molecular Formula: C₁₇H₂₅NO₅S
• Molecular Weight: 355.453
• Mol File: 128510-88-3.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 474.547 °C at 760 mmHg
• Flash Point: 240.798 °C
• Appearance: /
• Density: 1.197g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: 2-8°C
• PKA: -2.63±0.40(Predicted)
• CAS DataBase Reference: (R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE(128510-88-3)
• EPA Substance Registry System: (R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE(128510-88-3)

Safety Data

• Hazardous Substances Data: 128510-88-3(Hazardous Substances Data)

Usage

Uses

tert-Butyl (R)-2-[[[(4-Methylphenyl)sulfonyl]oxy]methyl]-1-pyrrolidinecarboxylate is an intermediate in the synthesis of (2S)-Ethylpyrrolidine Hydrochloride (E818080), which is used as a reagent in the synthesis of N,N''-substituted-1,3-diamino-2-hydroxypropanes for treating Alzheimer''s disease. Also used as a reagent in the synthesis of cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as JAK kinase inhibitors for treatment of autoimmune disease, cancer, inflammatory disease, and other diseases.

InChI:InChI=1/C17H25NO5S/c1-13-7-9-15(10-8-13)24(20,21)22-12-14-6-5-11-18(14)16(19)23-17(2,3)4/h7-10,14H,5-6,11-12H2,1-4H3

Upstream product

• 59378-81-3 1-(tert-butoxycarbonyl)prolin-2R-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 147-85-3 L-proline 
• 68832-13-3 D-prolinol 
• 344-25-2 D-Prolin 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 

Downstream Products

• 929917-65-7 (R)-2-(4-benzylaminophenoxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester 
• 929918-37-6 (R)-2-[4-(4-iodobenzoyl)phenoxymethyl]pyrrolidine-1-carboxylic acid tert-butyl ester 
• 929918-01-4 (R)-2-(4-benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 60419-23-0 (R)-(-)-1-(2-pyrrolidinylmethyl)pyrrolidine 
• 154887-98-6 (4R,6R)-conioidine A 
• 154887-98-6 (4R,6S)-conioidine A 
• 101555-60-6 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1006382-10-0 (R)-2-[4-(3-phenyl-prop-2-ynyloxy)-phenoxymethyl]-pyrrolidine hydrochloride 
• 1006382-09-7 (R)-2-(4-prop-2-ynyloxy-phenoxymethyl)-pyrrolidine hydrochloride 
• 1006382-20-2 (R)-2-(4-prop-2-ynyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1005736-95-7 (R)-2-(4-Pyrrol-1-yl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 942427-42-1 (R)-2-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 929917-73-7 (R)-2-[4-(4-chlorobenzyl)phenoxymethyl]pyrrolidine-1-carboxylic acid tert-butyl ester 
• 929918-39-8 (R)-2-(4-iodo-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis and Stereochemical Assignment of Conioidine A: DNA- And HSA-Binding Studies of the Four Diastereomers

Conioidine A (1), isolated in 1993 with unknown relative and absolute configuration, was suggested to be a DNA-binding compound by an indirect technique. Four stereoisomers of conioidine A have been synthesized from d- and l-proline, and the natural product has been identified as possessing (4R,6R) absolute configuration. Binding of the conioidine diastereomers to calf thymus DNA (CT DNA) and human serum albumin (HSA) has been investigated by fluorescence spectroscopy and isothermal titration calorimetry (ITC). All stereoisomers display at least an order of magnitude weaker binding to DNA than the control compound netropsin; however, a strong association with HSA was observed for the (4R,6S) stereoisomer.

AMINOPYRIDINE COMPOUNDS AND METHODS FOR THE PREPARATION AND USE THEREOF

The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its proteases arginine gingipain A/B (Rgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I and Formula III, as described herein, and pharmaceutically acceptable salts thereof.

Solvent free, fast and asymmetric Michael additions of ketones to nitroolefins using chiral pyrrolidine–pyridone conjugate bases as organocatalysts

New chiral organocatalysts are envisaged based on a pyrrolidine–pyridone conjugate and synthesized from commercially available proline employing standard protocols. These catalysts were found to be useful for asymmetric Michael additions of ketones to nitroolefins to afford the desired products in very good yields (up to 98%) with excellent diastereo- and enantioselectivities (>97:3 syn/anti and up to 98% ee) in very short reaction time compared with the existing reports.