(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid
• CAS No.: 2438-57-5
• Molecular Formula: C5H8FNO2
• Molecular Weight: 133.122
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10179130
• Nikkaji Number: J1.212.022B
• Wikidata: Q27454670
• Mol file: 2438-57-5.mol

Synonyms:(2S,4S)-4-fluoropyrrolidine-2-carboxylic acid;2438-57-5;6745-32-0;cis-4-Fluoroproline;C5H8FNO2;(2S,4S)-4-Fluoro-pyrrolidine-2-carboxylic acid;(4S)-4-fluoro-L-proline;L-Proline, 4-fluoro-, cis-;cis-4-Fluoro-L-proline;(2S,4S)-4-Fluoropyrrolidine-2-carboxylicAcid;L-PROLINE, 4-FLUORO-, (4S)-;(2S,4S)-4-FLUOROPROLINE;MFCD02683983;H-CIS-4-FLUORO-PRO-OH;21156-75-2;Proline, 4-fluoro-, cis-;SCHEMBL661917;H-CIS-PRO(4-F)-OH;rel-((2S,4R)-4-Fluoropyrrolidine-2-carboxylic acid),labeled with tritium;DTXSID10179130;L-Proline, 4-fluoro-,(4S)-;ZIWHMENIDGOELV-IMJSIDKUSA-N;AMY13595;BBL100867;STL554661;AKOS005063535;AB12545;AC-2247;DS-11725;CS-0058726;EN300-67319;A26505;(25,45)-4-fluoropyrrolidine-2-carboxylic acid;4-(S)-Fluoro-pyrrolidine-2-(S)-carboxylic acid;A817256;J-015483;J-501053;Q27454670

Chemical Property of (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 0.00271mmHg at 25°C
• Refractive Index: 1.472
• Boiling Point: 265.1 °C at 760 mmHg
• PKA: 1.88±0.40(Predicted)
• Flash Point: 114.1 °C
• PSA: 49.33000
• Density: 1.3 g/cm³
• LogP: 0.09980
• Storage Temp.: Store at RT.
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 133.05390666
• Heavy Atom Count: 9
• Complexity: 128

Purity/Quality:

97% ^*data from raw suppliers

cis-4-Fluoroproline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CNC1C(=O)O)F
• Isomeric SMILES: C1[C@@H](CN[C@@H]1C(=O)O)F
• Uses: cis-4-Fluoroproline is used in the study of stereoelectronic effects on collagen stability.

Technology Process of (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid

There total 20 articles about (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (203866-13-1) → (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,913820-71-0)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 8h;

Reference yield: 58.0%

(5S,7R)-7-fluoro-2,2-bis(trifluoromethyl)-1-aza-3-oxabicyclo<3.3.0>octan-4-one (156046-04-7) → (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,2507-61-1,7553-49-3,21156-44-5,21156-75-2,60828-35-5,131176-02-8,913820-71-0)

Guidance literature:

With water; In isopropyl alcohol; Ambient temperature;

DOI:10.1016/0022-1139(93)02907-V

Reference yield: 47.0%

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4) → (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid (2438-57-5,913820-71-0)

Guidance literature:

1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate; With trifluoroacetic acid; at 20 ℃; for 1.5h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; water; for 16h;

DOI:10.1002/anie.200803897

upstream raw materials:

methyl 1-acetyl-cis-4-fluoro-L-pyrrolidin-5-one-2-carboxylate

(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

4R-4-hydroxyproline

(6R,7aS)-6-hydroxy-3,3-bis(trifluoromethyl)tetrahydro-pyrrolo[1,2-c]oxazol-1-one

Downstream raw materials:

(2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-fluoropyrrolidine-2-carboxylic acid

(2S,4R)-N-Fmoc-4-fluoroproline

(2S,4R)-N-methyl-4-fluoropyrrolidine-2-carboxylic acid hydrochloride

4-oxo-L-proline