Bicyclo[2.2.2]octan-1-ol, acetate

Base Information

• Chemical Name: Bicyclo[2.2.2]octan-1-ol, acetate
• CAS No.: 56714-23-9
• Molecular Formula: C10H16O2
• Mol file: 56714-23-9.mol

Synonyms:

Chemical Property of Bicyclo[2.2.2]octan-1-ol, acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.2]octan-1-ol, acetate

There total 1 articles about Bicyclo[2.2.2]octan-1-ol, acetate 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:

bicyclo[2,2,2]octane (280-33-1) + acetic anhydride (108-24-7) → bicyclo[2.2.2]octan-2-one (2716-23-6) + Bicyclo<2.2.2>oct-1-yl-acetate (56714-23-9)

Guidance literature:

With pyridine; methyltrifluoromethyldioxirane; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, TFP, -22 deg C, 2 min, 2.) reflux, 0.5 h;

DOI:10.1021/ja00199a039

Reference yield:

Bicyclo<2.2.2>oct-1-yl-acetate (56714-23-9) → 1-(bicyclo[2.2.2]octan-1-yl) 3-methyl 5-amino-2-(8-methyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocin-2-yl)isophthalate

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hydroxide / water; methanol / 50 °C

2: dicyclohexyl-carbodiimide; dmap / dichloromethane / -15 - 20 °C / Inert atmosphere

3: sodium hydrogencarbonate; 2’-(dimethylamino)-2-biphenylyl-palladium(II)chloride dinorbornylphosphine complex / water; 1,2-dimethoxyethane / 16 h / 80 °C / Inert atmosphere; Sealed tube

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C / 775.74 Torr

With dmap; 2’-(dimethylamino)-2-biphenylyl-palladium(II)chloride dinorbornylphosphine complex; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; potassium hydroxide; In methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; 3: |Suzuki Coupling;

DOI:10.1002/chem.201901208

Reference yield:

Bicyclo<2.2.2>oct-1-yl-acetate (56714-23-9) → 5-((3-((bicyclo[2.2.2]octan-1-yloxy)carbonyl)-5-(methoxycarbonyl)-4-(8-methyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocin-2-yl)phenyl)amino)-5-oxopentanoic acid

Guidance literature:

Multi-step reaction with 5 steps

1: potassium hydroxide / water; methanol / 50 °C

2: dicyclohexyl-carbodiimide; dmap / dichloromethane / -15 - 20 °C / Inert atmosphere

3: sodium hydrogencarbonate; 2’-(dimethylamino)-2-biphenylyl-palladium(II)chloride dinorbornylphosphine complex / water; 1,2-dimethoxyethane / 16 h / 80 °C / Inert atmosphere; Sealed tube

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C / 775.74 Torr

5: dichloromethane / 16 h / 20 °C / Inert atmosphere

With dmap; 2’-(dimethylamino)-2-biphenylyl-palladium(II)chloride dinorbornylphosphine complex; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; potassium hydroxide; In methanol; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; 3: |Suzuki Coupling;

DOI:10.1002/chem.201901208

upstream raw materials:

bicyclo[2,2,2]octane

acetic anhydride

Refernces