3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester
• CAS No.: 956320-40-4
• Molecular Formula: C₃₃H₄₇ClN₂O₄Si
• Molecular Weight: 599.286
• Mol file: 956320-40-4.mol

Synonyms:3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

Chemical Property of 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

There total 10 articles about 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-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: 93.0%

trifluoro-methanesulfonic acid 3-chloro-4-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (956320-39-1) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (956320-40-4)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; at 60 - 80 ℃; for 1h;

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (956320-40-4)

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 / methanol; ethanol / 12 h / 20 °C

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

7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 1 h / 60 - 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; methanol; 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) → 3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (956320-40-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: hydrogen / palladium hydroxide on carbon / methanol; ethanol / 12 h / 20 °C

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

4: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 1 h / 60 - 80 °C

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

upstream raw materials:

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

4-methoxycarbonylphenylboronic acid

4-HYDROXYPIPERIDINE

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

Downstream raw materials:

3'-chloro-4'-[(R)-2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid