(3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester
• CAS No.: 188302-27-4
• Molecular Formula: C₁₄H₁₄FNO₄
• Molecular Weight: 279.268
• DSSTox Substance ID: DTXSID60572470
• Mol file: 188302-27-4.mol

Synonyms:(3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester

Chemical Property of (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 279.09068609
• Heavy Atom Count: 20
• Complexity: 417

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C(=O)CC(C(C1=O)C(=O)OC)C2=CC=C(C=C2)F

Technology Process of (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester

There total 8 articles about (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester 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: 32.0%

dimethyl-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-3,5-piperidinedicarboxylate (511284-18-7) → (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester (188302-27-4)

Guidance literature:

With water; subtilisin Carlsberg; In dimethyl sulfoxide; for 48h; pH=6.5; Product distribution / selectivity; Enzymatic reaction; potassium phosphate buffer;

Reference yield:

methyl cyanoformate (17640-15-2) + 4-(4-fluorophenyl)-1-methylpiperidine-2,6-dione (511283-89-9) → (3R,4S)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester + (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester (188302-27-4) + dimethyl-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-3,5-piperidinedicarboxylate (511284-18-7)

Guidance literature:

4-(4-fluorophenyl)-1-methylpiperidine-2,6-dione; With (R,S,S,R)-PhCH(Me)N(Li)CH(Ph)CH(Ph)N(Li)CH(Me)Ph; In tetrahydrofuran; hexane; at -78 ℃;

methyl cyanoformate; In tetrahydrofuran; hexane; at -78 - -40 ℃; Title compound not separated from byproducts;

DOI:10.1055/s-2002-35588

Reference yield:

4-fluorobenzaldehyde (459-57-4) → (3S,4R)-4-(4-fluorophenyl)-1-methyl-2,6-dioxopiperidine-3-carboxylic acid methyl ester (188302-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / piperidine / n-heptane / 3.5 h / Heating / reflux

2: potassium carbonate / acetic acid methyl ester / 18 h / Heating / reflux

3: water / subtilisin Carlsberg / acetone / 16 - 24 h / 40 °C / pH 6.0 - 6.5 / Enzymatic reaction

With water; potassium carbonate; acetic acid; piperidine; subtilisin Carlsberg; In n-heptane; acetic acid methyl ester; acetone;

upstream raw materials:

methyl cyanoformate

4-(4-fluorophenyl)-1-methylpiperidine-2,6-dione

dimethyl-4-(4-fluorophenyl)-1-methyl-2,6-dioxo-3,5-piperidinedicarboxylate

methyl 3-(methylamino)-3-oxopropanoate