(2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate
• CAS No.: 203866-16-4
• Molecular Formula: C11H18FNO4
• Molecular Weight: 247.267
• Hs Code.: 2933998090
• European Community (EC) Number: 610-364-8
• Nikkaji Number: J932.823H
• Mol file: 203866-16-4.mol

Synonyms:203866-16-4;(2S,4S)-1-TERT-BUTYL 2-METHYL 4-FLUOROPYRROLIDINE-1,2-DICARBOXYLATE;N-Boc-cis-4-Fluoro-L-proline methyl ester;1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate;1-O-tert-butyl 2-O-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate;475561-81-0;MFCD11054130;SCHEMBL91557;(2S,4S)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-;METPQQHVRNLTRX-YUMQZZPRSA-N;N-(tert-Butoxycarbonyl)-(2S,4S)-4-fluoroprolinemethylester;AKOS005259523;AKOS016008665;CS-W001496;DS-16715;A4437;AM20090158;N-BOC-(2S,4S)-4-fluoroproline methyl ester;EN300-7349843;N-Boc-cis-4-Fluoro-L-proline methyl ester, 97%;N-T-BOC-CIS-4-FLUORO-L-PROLINE METHYL ESTER;1-(tert-Butoxycarbonyl)-4alpha-fluoro-L-proline methyl ester;N-(tert-Butoxycarbonyl)-(2S,4S)-4-fluoroproline methyl ester;1-tert-butyl 2-methyl (2S,4S)-4-fluoro-1,2-pyrrolidinedicarboxylate;methyl(2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylate;1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-

Chemical Property of (2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 210 °C
• Refractive Index: 1.466
• Boiling Point: 296.525 °C at 760 mmHg
• PKA: -5.68±0.60(Predicted)
• Flash Point: 133.134 °C
• PSA: 55.84000
• Density: 1.168 g/cm³
• LogP: 1.44480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 247.12198622
• Heavy Atom Count: 17
• Complexity: 313

Purity/Quality:

96% ^*data from raw suppliers

Ethyl(2S,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)OC)F
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)OC)F

Technology Process of (2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

There total 23 articles about (2S,4S)-1-Tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate 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: 100.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

With diethylamino-sulfur trifluoride; In 1,2-dichloro-ethane; at -10 - 20 ℃; for 17.5h;

Reference yield: 85.0%

N-tert-butoxycarbonyl-trans-4-(trifluoromethylsulfonyloxy)-L-proline methyl ester (189160-59-6) → N-BOC-3,4-didehydro-(S)-proline methyl ester (74844-93-2) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

With tetrabutylammonium fluoride hydrofluoride; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo8015659

Reference yield: 85.0%

(2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (88043-21-4) → 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

With [Cu(2,9-dimethyl-1,10-phenanthroline)2]*-[HF₂]-; In acetonitrile; at 110 ℃; for 15h; Concentration; Schlenk technique; Inert atmosphere;

DOI:10.1021/om4008967

upstream raw materials:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

N-tert-butoxycarbonyl-trans-4-(trifluoromethylsulfonyloxy)-L-proline methyl ester

di-tert-butyl dicarbonate

(R)-4-hydroxy-L-proline ethyl ester

Downstream raw materials:

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

(2S,4S)-methyl 4-fluoropyrrolidine-2-carboxylate

tert-butyl (2S,4S)-4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(2R,4S)-2-allyl-4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Refernces

• 1、 -. "COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS". Page/Page column 271. . Retrieved 2021/09/11.
• 2、 Liu, Qingjie,Batt, Douglas G.,Weigelt, Carolyn A.,Yip, Shiuhang,Wu, Dauh-Rurng,Ruzanov, Max,Sack, John S.,Wang, Jinhong,Yarde, Melissa,Li, Sha,Shuster, David J.,Xie, Jenny H.,Sherry, Tara,Obermeier, Mary T.,Fura, Aberra,Stefanski, Kevin,Cornelius, Georgia,Khandelwal, Purnima,Tino, Joseph A.,Macor, John E.,Salter-Cid, Luisa,Denton, Rex,Zhao, Qihong,Dhar, T. G. Murali. "Novel Tricyclic Pyroglutamide Derivatives as Potent RORγt Inverse Agonists Identified using a Virtual Screening Approach". supporting information. p. 2510 - 2518. Retrieved 2020/12/03.