(3R,4S)-Ethyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate

Base Information

• Chemical Name: (3R,4S)-Ethyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate
• CAS No.: 109887-52-7
• Molecular Formula: C₁₅H₁₆FNO₄
• Molecular Weight: 293.295
• European Community (EC) Number: 600-930-2
• DSSTox Substance ID: DTXSID60595341
• Nikkaji Number: J2.560.867D
• Wikidata: Q72471386
• Mol file: 109887-52-7.mol

Synonyms:109887-52-7;(3R,4S)-Ethyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate;trans-3-Ethoxycarbonyl-4-(4-flurophenyl)-N-methyl piperdine-2,6-dione;Ethyl (3R,4S)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate;C15H16FNO4;SCHEMBL3924677;DTXSID60595341;AKOS005762907;TRANS-3-ETHOXY CARBONYL-4-(4-FLUOROPHENYL)-N-METHYL PIPERIDIN-2,6-DIONE;A894964;(3R,4S)-Ethyl4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate

Chemical Property of (3R,4S)-Ethyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate

Chemical Property:

• Vapor Pressure: 2E-07mmHg at 25°C
• Refractive Index: 1.526
• Boiling Point: 424.9 °C at 760 mmHg
• PKA: 8.69±0.40(Predicted)
• Flash Point: 210.7 °C
• PSA: 63.68000
• Density: 1.258 g/cm³
• LogP: 1.41520
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 293.10633615
• Heavy Atom Count: 21
• Complexity: 431

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3R,4S)-Ethyl4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(CC(=O)N(C1=O)C)C2=CC=C(C=C2)F
• Isomeric SMILES: CCOC(=O)[C@@H]1[C@H](CC(=O)N(C1=O)C)C2=CC=C(C=C2)F

Technology Process of (3R,4S)-Ethyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate

There total 20 articles about (3R,4S)-Ethyl 4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylate 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%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + C14H13FN2O → (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2,109887-52-7)

Guidance literature:

C₁₄H₁₃FN₂O; With C₃₁H₄₄N₄O₄; ytterbium(III) triflate; In dichloromethane; at 35 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

2-carboethoxy-N-methyl-acetamide; With triethylamine; In dichloromethane; at 40 ℃; for 72h; Reagent/catalyst; Solvent; Concentration; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201603056

Reference yield: 90.0%

methyl 3-(methylamino)-3-oxopropanoate (76311-95-0) + (E)-4-fluorocinnamic acid (459-32-5) → (3S,4R)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (188302-25-2,109887-52-7)

Guidance literature:

With cinchonidine; sodium hydride; In dimethyl sulfoxide; at -15 - 20 ℃; for 0.166667h; Reagent/catalyst;

Reference yield: 85.5%

2-carboethoxy-N-methyl-acetamide (71510-95-7) + p-fluorocinnamoyl-3,5-dimethyl-1H-pyrazole → (3R,4S)-3-ethoxycarbonyl-4-(4-fluorophenyl)-N-methylpiperidine-2,6-dione (109887-52-7)

Guidance literature:

2-carboethoxy-N-methyl-acetamide; p-fluorocinnamoyl-3,5-dimethyl-1H-pyrazole; With C₃₂H₄₆N₄O₄; ytterbium(III) triflate; In toluene; at 35 ℃; for 0.333333h;

With triethylamine; In toluene; at 30 - 50 ℃; Reagent/catalyst; Solvent;

upstream raw materials:

2-carboethoxy-N-methyl-acetamide

4-fluorobenzaldehyde

trans-3-ethoxycarbonyl-4(4'-fluorophenyl)piperidin-2,6-dione

methyl iodide

Downstream raw materials:

(3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylic acid phenyl ester

(3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine

Refernces

• 1、 -. "A synthetic Sparrow west sandbank chiral intermediates". Paragraph 0044-0046. . Retrieved 2017/07/18.
• 2、 -. "Intermediate for synthesizing paroxetine and preparation method for intermediate and use of intermediate". . . Retrieved 2016/10/08.