benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Base Information

• Chemical Name: benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate
• CAS No.: 1477524-36-9
• Molecular Formula: C₂₇H₂₈N₂O₃
• Molecular Weight: 428.531
• Mol file: 1477524-36-9.mol

Synonyms:benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Chemical Property of benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

There total 8 articles about benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)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: 43.0%

methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-10-9) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-36-9)

Guidance literature:

With titanium(IV) isopropylate; In neat (no solvent); at 130 ℃; Molecular sieve;

Reference yield:

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate (1477524-04-1) → benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-36-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / toluene; dichloromethane / 0.5 h / -78 °C

2.1: toluene-4-sulfonic acid / acetone; water / 1 h / 75 °C

3.1: sodium hydride / methanol / 0.5 h / 20 °C

3.2: 20 °C

4.1: sodium hydride / 1,4-dioxane / 0.67 h / 20 - 100 °C / Cooling with ice

5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane / 0.83 h / 120 °C / Microwave irradiation

7.1: titanium(IV) isopropylate / neat (no solvent) / 130 °C / Molecular sieve

With titanium(IV) isopropylate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium hydride; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination / 5.1: |Suzuki Coupling;

Reference yield:

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (1477524-05-2) → benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-36-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / acetone; water / 1 h / 75 °C

2.1: sodium hydride / methanol / 0.5 h / 20 °C

2.2: 20 °C

3.1: sodium hydride / 1,4-dioxane / 0.67 h / 20 - 100 °C / Cooling with ice

4.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane / 0.83 h / 120 °C / Microwave irradiation

6.1: titanium(IV) isopropylate / neat (no solvent) / 130 °C / Molecular sieve

With titanium(IV) isopropylate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; water; acetone; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination / 4.1: |Suzuki Coupling;

upstream raw materials:

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

4-(4-bromophenyl)-4-(hydroxymethyl)cyclohexan-1-one

methyl 2-(4-(4-bromophenyl)-4-(hydroxymethyl)cyclohexylidene)acetate

Downstream raw materials:

2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

benzyl 2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate