(2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate
• CAS No.: 203866-18-6
• Molecular Formula: C11H18FNO4
• Molecular Weight: 247.267
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00473199
• Nikkaji Number: J932.825D
• Wikidata: Q72476917
• Mol file: 203866-18-6.mol

Synonyms:203866-18-6;(2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate;N-BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER;1-tert-butyl 2-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate;(4R)-1-Boc-4-Fluoro-L-proline methyl ester;1-O-tert-butyl 2-O-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate;BOC-TRANS-4-FLUORO-L-PROLINE METHYL ESTER;MFCD07367993;SCHEMBL2995724;AMY3075;DTXSID00473199;METPQQHVRNLTRX-SFYZADRCSA-N;Methyl N-(tert-butoxycarbonyl)-(2S, 4R)-4-fluoroprolinate;1-(tert-butyl) 2-methyl (2S,4R)-4-fluoropyrrolidine-1,2-dicarboxylate;AKOS015961653;CS-W012681;AC-14451;AC-33231;AS-36306;N-Boc-trans-4-fluoro-L-prolinemethylester;EN300-7282689;A814513;J-013268;N-Boc-trans-4-fluoro-L-proline methyl ester, 97%;1-(tert-Butoxycarbonyl)-4beta-fluoro-L-proline methyl ester;(2S,4R)-2-methyl N-Boc-4-fluoro-pyrrolidine-2-carboxylate;1,2-Pyrrolidinedicarboxylicacid,4-fluoro-,1-(1,1-dimethylethyl)2-methyl ester,(2S,4R)-;1,2-Pyrrolidinedicarboxylic acid, 4-fluoro-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4R)-

Chemical Property of (2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

Chemical Property:

• Appearance/Colour: WHITE TO TAN SOLID, POWDER, CRYSTALS
• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: 36-39°C
• Refractive Index: 1.465
• Boiling Point: 296.525 °C at 760 mmHg
• Flash Point: 133.134 °C
• PSA: 55.84000
• Density: 1.168 g/cm³
• LogP: 1.44480
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• 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:

98%, ^*data from raw suppliers

N-Boc-trans-4-fluoro-L-proline methyl ester ^*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
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)OC)F
• Uses: N-Boc-trans-4-fluoro-L-proline methyl ester is used to prepare (S)-2-[N-(N'-benzyl-(S)-4-fluoro-L-prolyl)amino]benzophenone by reacting with of 2-aminobenzophenone in the presence of potassium tert -butoxide.

Technology Process of (2S,4R)-1-tert-Butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

There total 4 articles about (2S,4R)-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: 64.0%

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate (203866-18-6) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

With methanol; N-(2-chloro-1,1,2-trifluoroethyl)diethylamine; In chloroform; at 10 - 60 ℃; for 10 - 15h; Product distribution / selectivity;

Reference yield:

2-(((3S,5S)-1-(tert-butoxycarbonyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)oxy)-2-oxoacetic acid → methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate (203866-18-6) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

With disodium hydrogenphosphate; Ir[F(Me)ppy]2(dtbbpy)PF₆; Selectfluor; In water; acetone; at 30 ℃; for 4h; Overall yield = 79 %; Overall yield = 195 mg; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1016/j.tet.2019.05.043

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate (203866-18-6) + 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (203866-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 0 - 20 °C

2: Selectfluor; disodium hydrogenphosphate; Ir[F(Me)ppy]2(dtbbpy)PF₆ / water; acetone / 4 h / 30 °C / Inert atmosphere; Sealed tube; Irradiation

With disodium hydrogenphosphate; Ir[F(Me)ppy]2(dtbbpy)PF₆; Selectfluor; In diethyl ether; water; acetone;

DOI:10.1016/j.tet.2019.05.043

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

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

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

Downstream raw materials:

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

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

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

(2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid

Refernces

• 1、 -. "PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE FLUOROPROLINE DERIVATIVE". Page/Page column 10-11; 12-13. . Retrieved 2008/06/13.