benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate

Base Information

• Chemical Name: benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate
• CAS No.: 1273502-68-3
• Molecular Formula: C₂₆H₄₁N₃O₅
• Molecular Weight: 475.629
• Mol file: 1273502-68-3.mol

Synonyms:benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate

Chemical Property of benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate

There total 4 articles about benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate 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: 85.0%

benzyl (1S,2S)-1-[2-oxo-2-(piperidin-1-yl)ethylcarbamoyl]-2-methylbutylcarbamate (1273502-58-1) + pentan-3-one (96-22-0) → benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate (1273502-68-3)

Guidance literature:

benzyl (1S,2S)-1-[2-oxo-2-(piperidin-1-yl)ethylcarbamoyl]-2-methylbutylcarbamate; With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

pentan-3-one; In tetrahydrofuran; at 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1039/c0ob00628a

Reference yield:

piperidine (110-89-4) → benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate (1273502-68-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 0.17 h / 0 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 0.17 h / 0 °C / Inert atmosphere

4.1: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 4.2: Aldol condensation;

DOI:10.1039/c0ob00628a

Reference yield:

2-oxo-2-(piperidin-1-yl)ethyl-carbamic acid benzyl ester (3886-37-1) → benzyl (1S,2S)-1-[3-ethyl-3-hydroxy-1-oxo-1-(piperidin-1-yl)pentan-2-ylcarbamoyl]-2-methylbutylcarbamate (1273502-68-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / Inert atmosphere

2.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.17 h / 0 °C / Inert atmosphere

3.1: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 3.2: Aldol condensation;

DOI:10.1039/c0ob00628a

upstream raw materials:

piperidine

benzyl (1S,2S)-1-[2-oxo-2-(piperidin-1-yl)ethylcarbamoyl]-2-methylbutylcarbamate

pentan-3-one

2-oxo-2-(piperidin-1-yl)ethyl-carbamic acid benzyl ester

Refernces