rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane

Base Information

• Chemical Name: rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane
• CAS No.: 81521-85-9
• Molecular Formula: C₁₉H₃₅NO
• Molecular Weight: 293.493
• Mol file: 81521-85-9.mol

Synonyms:

Chemical Property of rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane

There total 6 articles about rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane 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: 71.0%

rel-(6S,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undec-1-ene (81497-18-9) → rel-(2R,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane (81521-84-8,74674-96-7) + rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane (81521-85-9,74674-96-7)

Guidance literature:

With aluminium hydride; In toluene; Yields of byproduct given; 1.) -72 deg , 5 h, 2.) 25 deg C, 14 h;

DOI:10.1021/ja00377a026

Reference yield:

6-Hydroxy-6-((E)-non-4-enyl)-piperidin-2-one (81521-86-0) → rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane (81521-85-9,74674-96-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 33 percent / 32 h / 25 °C

2: 0.95 g / phosphorus pentasulfide / benzene / 4 h / Heating

3: 91 percent / sodium hydroxide / methanol / 3 h / 25 °C

4: 100 percent / CH₂Cl₂ / 18 h / Ambient temperature

5: 1.) magnesium, 2.) magnesium chloride / 1.) ether, 2.) dichloromethane, reflux, 24 h

6: aluminum hydride / toluene / 1.) -72 deg , 5 h, 2.) 25 deg C, 14 h

With aluminium hydride; diphosphorus pentasulfide; sodium hydroxide; magnesium; magnesium chloride; In methanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja00377a026

Reference yield:

rel-(6S,7S,8S)-7-butyl-8-hydroxy-1-azaspiro<5.5>undecane-2-thione (81521-87-1) → rel-(2S,6R,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undecane (81521-85-9,74674-96-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CH₂Cl₂ / 18 h / Ambient temperature

2: 1.) magnesium, 2.) magnesium chloride / 1.) ether, 2.) dichloromethane, reflux, 24 h

3: aluminum hydride / toluene / 1.) -72 deg , 5 h, 2.) 25 deg C, 14 h

With aluminium hydride; magnesium; magnesium chloride; In dichloromethane; toluene;

DOI:10.1021/ja00377a026

upstream raw materials:

rel-(6S,7S,8S)-7-butyl-8-hydroxy-2-(4-pentenyl)-1-azaspiro<5.5>undec-1-ene

6-Hydroxy-6-((E)-non-4-enyl)-piperidin-2-one

rel-(6S,7S,8S)-7-butyl-8-hydroxy-1-azaspiro<5.5>undecane-2-thione

rel-(6S,7S,8S)-7-butyl-8-hydroxy-2-(methylthio)-1-azaspiro<5.5>undec-1-ene