(3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine

Base Information

• Chemical Name: (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine
• CAS No.: 1374647-14-9
• Molecular Formula: C₂₆H₂₉ClN₂
• Molecular Weight: 404.983
• Mol file: 1374647-14-9.mol

Synonyms:(3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine

Chemical Property of (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine

There total 7 articles about (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine 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: 63.0%

((2S,4S)-1-benzyl-4-(dibenzylamino)pyrrolidin-2-yl)methanol (1318128-74-3) → (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine (1374647-14-9)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 5h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201101829

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine (1374647-14-9)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / dichloromethane / 6 h / Inert atmosphere; Reflux

2: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3: tetrabutylammoniun azide / acetonitrile / 2 h / 55 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

5: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetonitrile / 4 h / 20 °C / Inert atmosphere

6: methanesulfonyl chloride; triethylamine / dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; potassium carbonate; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201101829

Reference yield:

(2S,4R)-1-benzyl-2-carbomethoxy-4-<(methylsulfonyl)oxy>pyrrolidine (114676-49-2) → (3R,5S)-1-benzyl-3-chloro-5-(dibenzylamino)piperidine (1374647-14-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrabutylammoniun azide / acetonitrile / 2 h / 55 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3: tetra-(n-butyl)ammonium iodide; potassium carbonate / acetonitrile / 4 h / 20 °C / Inert atmosphere

4: methanesulfonyl chloride; triethylamine / dichloromethane / 5 h / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; tetrabutylammoniun azide; tetra-(n-butyl)ammonium iodide; potassium carbonate; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/ejoc.201101829

upstream raw materials:

((2S,4S)-1-benzyl-4-(dibenzylamino)pyrrolidin-2-yl)methanol

(R)-4-hydroxy-L-proline ethyl ester

(2S,4R)-1-benzyl-4-hydroxyproline methyl ester

methyl (2S,4S)-4-azido-1-benzylpyrrolidine-2-carboxylate

Downstream raw materials:

(S)-1-benzyl-3-(dibenzylamino)piperidine

(3S,5R)-1-benzyl-3-(dibenzylamino)-5-methylpyrrolidine