(2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine

Base Information

• Chemical Name: (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine
• CAS No.: 547738-57-8
• Molecular Formula: C₂₂H₃₅NO₂
• Molecular Weight: 345.525
• Mol file: 547738-57-8.mol

Synonyms:(2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine

Chemical Property of (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine

There total 8 articles about (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine 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: 34.0%

(5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine (547738-53-4) → (2S,3R,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine (547738-59-0) + (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine (547738-57-8) + (2R,3R,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine

Guidance literature:

With hydrogen; acetic acid; platinum(IV) oxide; at 20 ℃; for 1h; atmospheric pressure;

DOI:10.1021/jo0341261

Reference yield:

(E)-2-ethyl-2-hexenoic acid (101489-01-4) → (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine (547738-57-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 85 percent / sulfuric acid / 72 h / 20 °C

2.1: n-BuLi / toluene / 1 h

2.2: toluene; tetrahydrofuran / 3.5 h / -78 - -40 °C

2.3: 67 percent / 2,6-di-tert-butyl-4-methylphenol / tetrahydrofuran; toluene / 1 h / -78 - 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 12 h / Heating

4.1: 1.8 g / H₂ / 20 percent Pd(OH)2/C / methanol / 12 h / 50 °C / 38000 Torr

5.1: 88 percent / K₂CO₃ / acetonitrile; H₂O / 10 h / 50 °C

6.1: triphenylphosphine; iodine; imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

7.1: 263 mg / triethylamine / acetonitrile / 15 h / Heating

8.1: 33 percent / acetic acid; H₂ / PtO₂ / 1 h / 20 °C / atmospheric pressure

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; hydrogen; iodine; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 2.2: Michael addition / 5.1: Michael addition;

DOI:10.1021/jo0341261

Reference yield:

(2S,3R)-3-amino-2-ethylhexanol (547738-49-8) → (2S,3S,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine (547738-57-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / K₂CO₃ / acetonitrile; H₂O / 10 h / 50 °C

2: triphenylphosphine; iodine; imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 263 mg / triethylamine / acetonitrile / 15 h / Heating

4: 33 percent / acetic acid; H₂ / PtO₂ / 1 h / 20 °C / atmospheric pressure

With 1H-imidazole; hydrogen; iodine; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; platinum(IV) oxide; In dichloromethane; water; acetonitrile; 1: Michael addition;

DOI:10.1021/jo0341261

upstream raw materials:

(5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propyl-1,4,5,6-tetrahydropyridine

(E)-2-ethyl-2-hexenoic acid

(2S,3R)-3-amino-2-ethylhexanol

2-ethylhex-2-enoic acid tert-butyl ester

Downstream raw materials:

(2S,3R,5R,6R)-2-(3'-benzyloxy)propyl-3-acetyl-5-ethyl-6-propylpiperidine