426844-76-0

Basic information

• Product Name: 1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine
• Synonyms: 1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine;(2S,4S)-1-Boc-2-cyano-4-fluoropyrrolidine;N-t-Boc-cis-4-Fluoro-L-prolinonitrile;(2S,4S)-tert-Butyl 2-cyano-4-fluoropyrrolidine-1-carboxylate;-tert-Butyl 2-cyano-4-fluoropyrrolidine-1-carboxylate;1-BOC-2-CYANO-4-FLUOROPYRROLIDINE;1-Pyrrolidinecarboxylic acid, 2-cyano-4-fluoro-, 1,1-dimethylethyl ester, (2S,4S)-
• CAS NO: 426844-76-0
• Molecular Formula: C₁₀H₁₅FN₂O₂
• Molecular Weight: 214.24
• Mol File: 426844-76-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 88-91°C
• Boiling Point: 316.7 ºC at 760 mmHg
• Flash Point: 145.4 ºC
• Appearance: White crystalline powder
• Density: 1.15 g/cm³
• Refractive Index: 1.472
• Storage Temp.: 2-8°C
• PKA: -7.30±0.60(Predicted)
• CAS DataBase Reference: 1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine(426844-76-0)
• EPA Substance Registry System: 1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine(426844-76-0)

Safety Data

• Statements: 43
• Safety Statements: 36/37
• RIDADR: UN3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 426844-76-0(Hazardous Substances Data)

Usage

General Description

1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine, also known as 4-Fluoropyrrolidin-2-carbonitrile N-Boc protected, is a chemical compound with potential applications in the pharmaceutical industry. It is a fluorinated pyrrolidine derivative that contains a cyano group and is protected with a 1-boc (tert-butyloxycarbonyl) group. 1-Boc-(2S,4S)-2-cyano-4-fluoropyrrolidine has the potential to be used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its unique structure and properties. It is important for its potential contributions to medicinal chemistry and drug discovery research.

InChI:InChI=1/C10H15FN2O2/c1-10(2,3)15-9(14)13-6-7(11)4-8(13)5-12/h7-8H,4,6H2,1-3H3/t7-,8-/m0/s1

Upstream product

• 203866-16-4 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Relevant articles and documents

Design, synthesis and biological evaluation of hetero-aromatic moieties substituted pyrrole-2-carbonitrile derivatives as dipeptidyl peptidase IV inhibitors

A series of novel hetero-aromatic moieties substituted α-amino pyrrole-2-carbonitrile derivatives was designed and synthesized based on structure-activity relationships (SARs) of pyrrole-2-carbonitrile inhibitors. All compounds demonstrated good dipeptidyl peptidase IV (DPP4) inhibitory activities (IC50 = 0.004-113.6 μM). Moreover, compounds 6h (IC50 = 0.004 μM) and 6n (IC50 = 0.01 μM) showed excellent inhibitory activities against DPP4, good selectivity (compound 6h, selective ratio: DPP8/DPP4 = 450.0; DPP9/DPP4 = 375.0; compound 6n, selective ratio: DPP8/DPP4 = 470.0; DPP9/DPP4 = 750.0) and good efficacy in an oral glucose tolerance test in ICR mice. Furthermore, compounds 6h and 6n demonstrated moderate PK properties (compound 6h, F% = 37.8%, t1/2 = 1.45 h; compound 6n, F% = 16.8%, t1/2 = 3.64 h).

Synthesis and biological evaluation of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2-carbonitrile derivatives as dipeptidyl peptidase-4 inhibitors for the treatment of type 2 diabetes

A novel series of pyrrolidine-2-carbonitrile and 4-fluoropyrrolidine-2- carbonitrile derivatives was designed, synthesized, and found to act as dipeptidyl peptidase-4 (DPP-4) inhibitors. From this series of compounds, compound 17a was identified as an efficacious, safe, and selective inhibitor of DPP-4. In vivo studies in ICR and KKAy mice showed that administration of this compound resulted in decreased blood glucose in these mice after an oral glucose challenge. Compound 17a showed high DPP-4 inhibitory activity (IC50 = 0.017 μM), moderate selectivity against DPP-4 (selective ratio: DPP-8/DPP-4 = 1324; DPP-9/DPP-4 = 1164), and good efficacy in oral glucose tolerance tests in ICR and KKAy mice. These in vivo anti-diabetic properties and its desirable pharmacokinetic profile in Sprague-Dawley rats demonstrate that compound 17a is a promising candidate for development as an anti-diabetic agent.