(S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate
• CAS No.: 203866-17-5
• Molecular Formula: C11H17 F2 N O4
• Molecular Weight: 265.257
• Hs Code.: 2933990090
• European Community (EC) Number: 805-080-8
• DSSTox Substance ID: DTXSID90456299
• Nikkaji Number: J932.824F
• Wikidata: Q72503556
• ChEMBL ID: CHEMBL4924940
• Mol file: 203866-17-5.mol

Synonyms:203866-17-5;(S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate;N-BOC-4,4-DIFLUORO-L-PROLINE METHYL ESTER;1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate;BOC-4,4-DIFLUORO-L-PROLINE METHYL ESTER;1-O-tert-butyl 2-O-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate;MFCD03094918;SCHEMBL706243;CHEMBL4924940;AMY3074;DTXSID90456299;BCP21719;1-(tert-butyl) 2-methyl (S)-4,4-difluoropyrrolidine-1,2-dicarboxylate;AKOS015920188;CS-W001497;DS-16679;A850871;N-Boc-4,4-Difluoro-L-proline methyl ester, 97%;J-013267;1-(tert-Butoxycarbonyl)-4,4-difluoro-L-proline methyl ester;(S)-4,4-Difluoro-N-Boc-pyrrolidine-2-carboxylic acid methyl ester;1-tert-butyl 2-methyl(2s)-4,4-difluoropyrrolidine-1,2-dicarboxylate;(S)-4,4-difluoro-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;1,2-Pyrrolidinedicarboxylicacid,4,4-difluoro-,1-(1,1-dimethylethyl)2-methyl ester,(2S)-;Methyl (2S)-N-(tert-butyloxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylate;TERT-BUTYL (2S)-2-(METHOXYCARBONYL)-4,4-DIFLUOROPYRROLIDINE-1-CARBOXYLATE;N-Boc-4,4-difluoro-L-proline Methyl Ester;1,2-Pyrrolidinedicarboxylic acid, 4,4-difluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S)-

Chemical Property of (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 41-46oC
• Boiling Point: 292.7ºCat 760 mmHg
• PKA: -8.00±0.60(Predicted)
• Flash Point: 130.8 ºC
• PSA: 55.84000
• Density: 1.22 g/cm³
• LogP: 1.74200
• Storage Temp.: Store at 0-5°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 265.11256435
• Heavy Atom Count: 18
• Complexity: 351

Purity/Quality:

98%, ^*data from raw suppliers

(S)-1-Tert-Butyl2-Methyl4,4-Difluoropyrrolidine-1,2-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-1,2-dicarboxylate

There total 11 articles about (S)-1-tert-butyl 2-methyl 4,4-difluoropyrrolidine-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: 99.0%

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → 1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate (203866-17-5)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20 ℃; for 2.16667h;

Reference yield: 95.0%

1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline (203866-15-3) + methyl iodide (74-88-4) → 1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate (203866-17-5)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 16h; Inert atmosphere;

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate (203866-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 93 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

3: 90 percent / DAST / CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2003.08.075

upstream raw materials:

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

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

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4,4-difluoro-pyrrolidine-2-carboxylic acid

(S)-2-carbamoyl-4,4-difluoropyrrolidine-1-carboxylic acid tert-butyl ester

(S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate

tert-butyl (S)-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamate

Refernces

• 1、 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.
• 2、 -. "BENZIMIDAZOLE-LINKED INDOLE COMPOUND ACTING AS NOVEL DIVALENT IAP ANTAGONIST". Paragraph 0272; 0274. . Retrieved 2019/03/14.