benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate

Base Information

• Chemical Name: benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate
• CAS No.: 1446127-76-9
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.39
• Mol file: 1446127-76-9.mol

Synonyms:benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate

Chemical Property of benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate

There total 8 articles about benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate 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: 52.0%

(Z)-benzyl 2-(but-1-enyl)piperidine-1-carboxylate → benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate (1446127-76-9) + benzyl (2S)-2-[(2S)-2-hydroxybutyl]piperidine-1-carboxylate (190383-64-3)

Guidance literature:

(Z)-benzyl 2-(but-1-enyl)piperidine-1-carboxylate; With mercury(II) diacetate; In tetrahydrofuran; water; at 20 ℃;

With sodium tetrahydroborate; sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h; Overall yield = 66 %; regioselective reaction;

DOI:10.1055/s-0036-1589523

Reference yield:

benzyl (2S)-2-(2-oxobutyl)piperidine-1-carboxylate → benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate (1446127-76-9) + benzyl (2S)-2-[(2S)-2-hydroxybutyl]piperidine-1-carboxylate (190383-64-3)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 8h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.055

Reference yield:

(S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (212557-00-1) → benzyl (2S)-2-[(2R)-2-hydroxybutyl]piperidine-1-carboxylate (1446127-76-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride; triethylamine; dimethyl sulfoxide / dichloromethane / -78 °C

2.1: potassium hydroxide / methanol / 1 h / 20 °C

3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.67 h / 0 °C

4.1: sodium tetrahydroborate / methanol / 2 h / 20 °C

4.2: 18 h / 20 °C

5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 8 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; methanesulfonyl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1.1: |Swern Oxidation / 2.1: |Henry Nitro Aldol Condensation / 3.1: |Henry Nitro Aldol Condensation / 4.1: |Nef Reaction;

DOI:10.1016/j.tet.2013.05.055

upstream raw materials:

pipecolinic acid

benzyl (2S)-2-[(1E)-2-nitrobut-1-en-1-yl]piperidine-1-carboxylate

(S)-pipecolinol

(S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester