3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane

Base Information

• Chemical Name: 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane
• CAS No.: 1360460-75-8
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• Mol file: 1360460-75-8.mol

Synonyms:3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane

Chemical Property of 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane

There total 8 articles about 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane 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: 39.0%

3β-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-8-azabicyclo[3.2.1]octane (1360460-74-7) → 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane (1360460-75-8)

Guidance literature:

With borane-THF; In tetrahydrofuran; for 0.75h; Cooling with ice; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.12.008

Reference yield:

2-bromo-1-(3,5-dihydroxyphenyl)ethan-1-one (62932-92-7) → 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane (1360460-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C

2: borane-THF / tetrahydrofuran / 0.75 h / Cooling with ice; Inert atmosphere

With borane-THF; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.bmcl.2011.12.008

Reference yield:

tropinone (532-24-1) → 3β-benzoyloxy-8-(2-hydroxy-2-(3,5-dihydroxyphenyl)ethyl)-8-azabicyclo[3.2.1]-octane (1360460-75-8)

Guidance literature:

Multi-step reaction with 6 steps

1: aluminum isopropoxide / isopropyl alcohol / 24.75 h / Reflux

2: triethylamine / toluene / 4 h / Reflux

3: 1,2-dichloro-ethane / 19 h / Cooling with ice; Inert atmosphere; Reflux

4: methanol / 22 h / 20 °C / Reflux

5: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C

6: borane-THF / tetrahydrofuran / 0.75 h / Cooling with ice; Inert atmosphere

With borane-THF; aluminum isopropoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; isopropyl alcohol; toluene; acetonitrile; 1: Meerwein-Ponndorf-Verley reduction;

DOI:10.1016/j.bmcl.2011.12.008

upstream raw materials:

3β-benzoyloxy-8-(2-(3,5-dihydroxyphenyl)-2-oxoethyl)-8-azabicyclo[3.2.1]octane

tropinone

3,5-dihydroxyacetophenone

2-bromo-1-(3,5-dihydroxyphenyl)ethan-1-one

Refernces