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

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

Used in Pharmaceutical Synthesis:
(R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE is used as an intermediate in the synthesis of (2S)-Ethylpyrrolidine Hydrochloride (E818080) for the treatment of Alzheimer's disease. It plays a crucial role in the development of this drug, contributing to its effectiveness in managing the cognitive decline associated with the condition.
Used in Alzheimer's Disease Treatment:
In the pharmaceutical industry, (R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE is used as a reagent in the synthesis of N,N''-substituted-1,3-diamino-2-hydroxypropanes. These compounds are integral in the development of drugs aimed at treating Alzheimer's disease, providing potential therapeutic benefits for patients suffering from this neurodegenerative condition.
Used in JAK Kinase Inhibitors Synthesis:
(R)-TERT-BUTYL 2-(TOSYLOXYMETHYL)PYRROLIDINE-1-CARBOXYLATE is also used as a reagent in the synthesis of cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives. These compounds act as JAK kinase inhibitors, which are utilized in the treatment of various diseases, including autoimmune diseases, cancer, and inflammatory conditions. The compound's role in this process highlights its importance in the development of targeted therapies for a range of medical conditions.

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

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

Downstream Products

• 60419-23-0 (R)-(-)-1-(2-pyrrolidinylmethyl)pyrrolidine 
• 101555-60-6 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 154887-98-6 (4R,6S)-conioidine A 
• 154887-98-6 (4R,6R)-conioidine A 
• 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 
• 929918-01-4 (R)-2-(4-benzyloxy-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 
• 929917-25-9 (R)-2-(4-benzylphenoxymethyl)-1-BOC-pyrrolidine 
• 1201786-39-1 C₂₇H₃₁NO₃S 

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.

Pyrrolidine-Oxadiazolone Conjugates as Organocatalysts in Asymmetric Michael Reaction

Pyrrolidine-oxadiazolone based organocatalysts are envisaged, synthesized, and utilized for asymmetric Michael reactions. Results of the investigations suggest that some of the catalysts are indeed efficient for stereoselective 1,4-conjugated Michael additions (dr: >97:3, ee up to 99%) in high chemical yields (up to 97%) often in short reaction time. As an extension, one enantiopure Michael adduct has been utilized to synthesize optically active octahydroindole.

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.

Enantioselective Synthesis of 6,6-Disubstituted Pentafulvenes Containing a Chiral Pendant Hydroxy Group

Simple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl function of a 1,2-formylacetophenone, followed by cyclization of a resulting fulvene-stabilized carbanion with the formyl group, generates bicyclic chiral alcohols with initial er values up to 94:6. Exceptional enantio-enrichment of the resultant alcohols results upon crystallization—even near racemic samples spontaneously de-racemize. This enables new families of substituted cyclopentadienes that are both enantiomerically and diastereomerically pure to be rapidly attained.

FUMAGILLOL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

Disclosed herein, in part, are fumagillol compounds and methods of use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making fumagillol compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

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.

5-AMINO-4-CARBAMOYL-PYRAZOLE COMPOUNDS AS SELECTIVE AND IRREVERSIBLE T790M OVER WT-EGFR KINASE INHIBITORS AND USE THEREOF????

Disclosed are compounds of Formula (I), pharmaceutical compositions comprising the same, processes for the preparation thereof, and the use thereof.

METHODS OF TREATING LIVER DISEASES

The invention provides tricyclic compounds and their use in treating liver disorders, such as non-alcoholic steatohepatitis and related disorders (e.g., fibrosis). The compounds are contemplated to have activity against methionyl aminopeptidase 2.

PARTIALLY SATURATED TRICYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

The invention provides tricyclic compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

Discovery of 4-[(2S)-2-{[4-(4-Chlorophenoxy)phenoxy]methyl}-1-pyrrolidinyl] butanoic acid (DG-051) as a novel leukotriene A4 hydrolase inhibitor of leukotriene B4 biosynthesis

Both in-house human genetic and literature data have converged on the identification of leukotriene 4 hydrolase (LTA4H) as a key target for the treatment of cardiovascular disease. We combined fragmentbased crystallography screening with an iterative medicinal chemistry effort to optimize inhibitors of LTA4H. Ligand efficiency was followed throughout our structure-activity studies. As applied within the context of LTA4H inhibitor design, the chemistry team was able to design a potent compound 20 (DG-051) (Kd=26 nM) with high aqueous solubility (>30 mg/mL) and high oral bioavailability (>80% across species) that is currently undergoing clinical evaluation for the treatment of myocardial infarction and stroke. The structural biology-chemistry interaction described in this paper provides a sound alternative to conventional screening techniques. This is the first example of a gene-to-clinic paradigm enabled by a fragment-based drug discovery effort.