(R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile

Base Information

• Chemical Name: (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile
• CAS No.: 956320-17-5
• Molecular Formula: C₃₂H₄₂Cl₂FN₃O₂Si
• Molecular Weight: 618.694
• Mol file: 956320-17-5.mol

Synonyms:(R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile

Chemical Property of (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile

There total 10 articles about (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile 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-cyano-3-fluorophenyl)boronic acid (843663-18-3) + (R)-trifluoro-methanesulfonic acid 3,5-dichloro-4-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (956320-18-6) → (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile (956320-17-5)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; at 80 ℃; for 1h;

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile (956320-17-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetic acid; sodium nitrite / water / 5.83 h / 0 - 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / Heating / reflux

2.2: 0.17 h / 0 - 20 °C

3.1: sodium tris(acetoxy)borohydride / 1,1-dichloroethane / 22 h / 20 - 55 °C

4.1: pyridine / dichloromethane / 12 h / 0 - 20 °C

5.1: hydrogen / palladium hydroxide on carbon / ethanol / 2 h / 20 °C / 1034.32 Torr

6.1: pyridine / dichloromethane / 2 h / 0 - 20 °C

7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 1 h / 80 °C

With pyridine; lithium aluminium tetrahydride; hydrogen; sodium tris(acetoxy)borohydride; sodium carbonate; acetic acid; sodium nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium hydroxide on carbon; In tetrahydrofuran; 1,1-dichloroethane; ethanol; dichloromethane; water; 7.1: Suzuki Coupling;

Reference yield:

(R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one (956320-30-2) → (R)-3',5'-dichloro-3-fluoro-4'-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carbonitrile (956320-17-5)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / dichloromethane / 12 h / 0 - 20 °C

2: hydrogen / palladium hydroxide on carbon / ethanol / 2 h / 20 °C / 1034.32 Torr

3: pyridine / dichloromethane / 2 h / 0 - 20 °C

4: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 1 h / 80 °C

With pyridine; hydrogen; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium hydroxide on carbon; In tetrahydrofuran; ethanol; dichloromethane; water; 4: Suzuki Coupling;

upstream raw materials:

(4-cyano-3-fluorophenyl)boronic acid

(R)-trifluoro-methanesulfonic acid 3,5-dichloro-4-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenyl ester

4-HYDROXYPIPERIDINE

(R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-1-(4-hydroxy-piperidin-1-yl)-pyrrolidin-2-one

Downstream raw materials:

(R)-3-[4-(3-amino-benzo[d]isoxazol-6-yl)-2,6-dichloro-benzyl]-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-2-one