2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile

Base Information

• Chemical Name: 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile
• CAS No.: 749929-13-3
• Molecular Formula: C₂₂H₂₆FNO₃
• Molecular Weight: 371.452
• Mol file: 749929-13-3.mol

Synonyms:2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile

Chemical Property of 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile

There total 5 articles about 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile 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:

(4-bromo-2-fluorophenyl)acetonitrile (114897-91-5) → 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile (749929-13-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium t-butanolate / tetrahydrofuran; N,N-dimethyl-formamide / 19 h / -10 - 11 °C / Inert atmosphere; Large scale

2: palladium; copper(l) iodide / Inert atmosphere

3: palladium; hydrogen

4: sodium hydroxide / methanol / Inert atmosphere

With copper(l) iodide; hydrogen; palladium; sodium hydroxide; sodium t-butanolate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling / 3: |Sonogashira Cross-Coupling / 4: |Sonogashira Cross-Coupling;

DOI:10.1021/op0600761

Reference yield:

2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile (749928-78-7) → 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile (749929-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium; hydrogen

2: sodium hydroxide / methanol / Inert atmosphere

With hydrogen; palladium; sodium hydroxide; In methanol; 1: |Sonogashira Cross-Coupling / 2: |Sonogashira Cross-Coupling;

DOI:10.1021/op0600761

Reference yield:

2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybutyl]-2-fluorophenyl}-2-methyl-propionitrile (749928-76-5) → 2-{4-[2-(2-cyclopentyl-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile (749929-13-3)

Guidance literature:

With sodium hydroxide; In methanol; Inert atmosphere;

DOI:10.1021/op0600761

upstream raw materials:

2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybut-1-ynyl]-2-fluoro-phenyl}-2-methyl-propionitrile

2-{4-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxybutyl]-2-fluorophenyl}-2-methyl-propionitrile

(4-bromo-2-fluorophenyl)acetonitrile

4-bromo-2-fluorobenzyl bromide