21156-44-5

Basic information

• Product Name: (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid
• Synonyms: (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid;(2S,4R)-4-Fluoro-2-pyrrolidinecarboxylic acid;(4R)-4-Fluor-L-prolin;(2S,4R)-4-fluoro-2-proline;trans-4-Fluoropyrrolidine-2-carboxylic acid
• CAS NO: 21156-44-5
• Molecular Formula: C₅H₈FNO₂
• Molecular Weight: 133.12
• Product Categories: Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 21156-44-5.mol

Chemical Properties

• Boiling Point: 265.108°C at 760 mmHg
• Flash Point: 114.133°C
• Appearance: /
• Density: 1.309g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.473
• Storage Temp.: 2-8°C
• PKA: 1.88±0.40(Predicted)
• CAS DataBase Reference: (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid(21156-44-5)
• EPA Substance Registry System: (2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid(21156-44-5)

Safety Data

• Hazardous Substances Data: 21156-44-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid is used as a chiral building block and a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable component in the development of new drugs with improved efficacy and selectivity.
Used in Chemical Research:
(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid is used as a versatile building block in organic synthesis, enabling the creation of complex organic molecules with potential applications in various industries, such as materials science, agrochemicals, and specialty chemicals.
Used in Chiral Scaffold Design:
(2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid serves as a chiral scaffold in the design of new chemical entities, allowing for the development of enantioselective catalysts and ligands, which are essential in asymmetric synthesis and other stereoselective chemical transformations.

InChI:InChI=1/C5H8FNO2/c6-3-1-4(5(8)9)7-2-3/h3-4,7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

Upstream product

• 618-27-9 hydroxy L-proline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 203866-18-6 methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate 
• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 148429-59-8 (6S,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one 
• 203866-14-2 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid 
• 156046-04-7 (5S,7R)-7-fluoro-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo<3.3.0>octan-4-one 

Downstream Products

• 203866-20-0 (2S,4R)-N-Fmoc-4-fluoroproline 
• 1443240-81-0 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{(1S,4R)-4-[3-((2S,4R)-4-fluoro-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea 
• 1007878-14-9 (2S,4R)-N-methyl-4-fluoropyrrolidine-2-carboxylic acid hydrochloride 

Relevant articles and documents

HETEROCYCLYL SUBSTITUTED PYRROLOPYRIDINES THAT ARE INHIBITORS OF THE CDK12 KINASE

This invention relates to compounds that are inhibitors of the CDK12 kinase. The compounds are useful in the treatment of disorders mediated by CDK12 kinase including myotonic dystrophy type 1 (DM1) and other disorders caused by the generation of RNA repeat expansion transcripts. In particular,the invention relates to compounds of the formula (I), or a pharmaceutically acceptable salts or N-oxides thereof, wherein R1a, R2, R3, R4a, R4b and R4c are as defined herein.

Synthesis of n.c.a. cis- and trans-4-[18F]fluoro-L-proline, radiotracers for PET-investigation of disordered matrix protein synthesis

A radiosynthesis of n.c.a. (2S,4R)-4-[18F]fluoroproline (trans-configuration) and its diastereomer (2S,4S)-4-[18F]fluoroproline (cis-configuration) has been developed. It allows the routine production of up to 18 GBq of product for c

Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline

Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.

Synthesis of (2S)-4,4-difluoroproline, (2S,4R)-4-fluoroproline and their derivatives from (S)-aspartic acid

Syntheses for (2S)-4,4-difluoroproline, (2S,4R)-4-fluoroproline and their derivatives are described starting from (S)-aspartic acid, using hexafluoroacetone as the protecting reagent and DAST as the fluorinating agent.