1H-Pyrrole, 4-(2,5-difluorophenyl)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5 -dihydro-2-phenyl-, (2S)-

Base Information

• Chemical Name: 1H-Pyrrole, 4-(2,5-difluorophenyl)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5 -dihydro-2-phenyl-, (2S)-
• CAS No.: 845256-48-6
• Molecular Formula: C23H29F2NOSi
• Molecular Weight: 401.572
• Mol file: 845256-48-6.mol

Synonyms:

Chemical Property of 1H-Pyrrole, 4-(2,5-difluorophenyl)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5 -dihydro-2-phenyl-, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrrole, 4-(2,5-difluorophenyl)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5 -dihydro-2-phenyl-, (2S)-

There total 32 articles about 1H-Pyrrole, 4-(2,5-difluorophenyl)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5 -dihydro-2-phenyl-, (2S)- 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:

C17H15F2NO + tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-4-(2,5-difluorophenyl)-2-phenyl-2-[(1,1,2,2-tetramethylpropoxy)methyl]-2,5-dihydro-1H-pyrrole (845256-48-6)

Guidance literature:

With 1H-imidazole; In dichloromethane;

Reference yield:

4-Allyl-4-phenyl-1,3-oxazolidin-2-one (686320-23-0) → (2S)-4-(2,5-difluorophenyl)-2-phenyl-2-[(1,1,2,2-tetramethylpropoxy)methyl]-2,5-dihydro-1H-pyrrole (845256-48-6) + (R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole

Guidance literature:

Multi-step reaction with 10 steps

1.1: ozone / dichloromethane / -78 °C

1.2: 20 °C

2.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 4 h

3.1: hydrogenchloride / 20 - 35 °C / Heating / reflux

4.1: sodium hydride / tetrahydrofuran / 0 - 20 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C

5.3: 24 h / 100 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 - 3 h / -78 - 0 °C

6.2: 1.5 h / -78 - 20 °C

7.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 3 - 3.02 h / 90 °C

8.1: sodium hydroxide; ethanol; water / 3 h / 20 - 60 °C

9.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 15 h

10.1: hexanes; diethylamine; isopropyl alcohol / Resolution of racemate

With 1H-imidazole; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; ethanol; water; sodium hexamethyldisilazane; sodium hydride; sodium carbonate; ozone; lithium chloride; lithium hexamethyldisilazane; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexanes; 1,2-dimethoxyethane; dichloromethane; water; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol; tert-butyl alcohol; 7.1: Suzuki Coupling;

Reference yield:

α-allylphenylglycine ethyl ester (193421-73-7) → (2S)-4-(2,5-difluorophenyl)-2-phenyl-2-[(1,1,2,2-tetramethylpropoxy)methyl]-2,5-dihydro-1H-pyrrole (845256-48-6) + (R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 20 °C / Heating / reflux

2.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C

3.1: sodium periodate / ruthenium trichloride / dichloromethane; water; acetonitrile / 5 h / 20 °C

4.1: hydrogenchloride / 20 - 35 °C / Heating / reflux

5.1: sodium hydride / tetrahydrofuran / 0 - 20 °C

6.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C

6.3: 24 h / 100 °C

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 - 3 h / -78 - 0 °C

7.2: 1.5 h / -78 - 20 °C

8.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane; water / 3 - 3.02 h / 90 °C

9.1: sodium hydroxide; ethanol; water / 3 h / 20 - 60 °C

10.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 15 h

11.1: hexanes; diethylamine; isopropyl alcohol / Resolution of racemate

With 1H-imidazole; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; ethanol; water; sodium hexamethyldisilazane; sodium hydride; sodium carbonate; triethylamine; lithium chloride; lithium hexamethyldisilazane; hydrogenchloride; ruthenium trichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexanes; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 8.1: Suzuki Coupling;

upstream raw materials:

tert-butyldimethylsilyl chloride

6-(2,5-difluorophenyl)-7a-phenyl-5,7a-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-3-one

methyl 4-methylene-2-phenylpyrrolidine-2-carboxylate

6-methylene-7a-phenyltetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one

Downstream raw materials:

(2S)-4-(2,5-difluorophenyl)-2-(hydroxymethyl)-N,N-dimethyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide

C₂₀H₁₈F₂N₂O₂

C₂₃H₂₄F₂N₂O₃

C₂₂H₂₄F₂N₂O₂