(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one

Base Information

• Chemical Name: (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one
• CAS No.: 660861-59-6
• Molecular Formula: C₂₆H₂₉NO₃
• Molecular Weight: 403.521
• Mol file: 660861-59-6.mol

Synonyms:(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one

Chemical Property of (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one

There total 4 articles about (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one 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: 85.0%

(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-45-0) → (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-59-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; at 20 ℃; for 24h; normal pressure;

DOI:10.3987/com-03-s40

Reference yield:

(1R,5R)-5,8,8-Trimethyl-2-oxo-3-oxa-bicyclo[3.2.1]octane-1-carbonyl chloride (502897-36-1) → (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-59-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4.985 g / Bu₃SnH / CH₂Cl₂ / 16 h / -78 - 20 °C

2.1: Ph₃C(+)BF₄(-) / CH₂Cl₂ / 16 h / 20 °C

2.2: CH₂Cl₂; tetrahydrofuran / 2 h / -78 °C

3.1: 85 percent / H₂ / 10 percent Pd/C / methanol; ethyl acetate / 24 h / 20 °C / normal pressure

With hydrogen; tri-n-butyl-tin hydride; trityl tetrafluoroborate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.3987/com-03-s40

Reference yield:

5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carboxylic acid (183850-84-2) → (1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (COCl)2; DMF / CH₂Cl₂ / 3.25 h / 0 - 20 °C

2.1: 4.985 g / Bu₃SnH / CH₂Cl₂ / 16 h / -78 - 20 °C

3.1: Ph₃C(+)BF₄(-) / CH₂Cl₂ / 16 h / 20 °C

3.2: CH₂Cl₂; tetrahydrofuran / 2 h / -78 °C

4.1: 85 percent / H₂ / 10 percent Pd/C / methanol; ethyl acetate / 24 h / 20 °C / normal pressure

With oxalyl dichloride; hydrogen; tri-n-butyl-tin hydride; trityl tetrafluoroborate; N,N-dimethyl-formamide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.3987/com-03-s40

upstream raw materials:

(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one

5,8,8-trimethyl-2-oxo-3-oxabicyclo[3.2.1]octane-1-carboxylic acid

(1R,5R)-5,8,8-Trimethyl-2-oxo-3-oxa-bicyclo[3.2.1]octane-1-carbonyl chloride

(1S,5R)-1-[(1,2-dihydroisoquinolin-2-yl)carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one

Downstream raw materials:

(R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline