(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2-dihydroisoquinolin-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-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one
• CAS No.: 660861-45-0
• Molecular Formula: C₂₆H₂₇NO₃
• Molecular Weight: 401.505
• Mol file: 660861-45-0.mol

Synonyms:(1S,5R)-5,8,8-trimethyl-1-[(1R)-1-phenyl-1,2-dihydroisoquinolin-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-dihydroisoquinolin-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-dihydroisoquinolin-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-dihydroisoquinolin-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:

phenylmagnesium chloride (100-59-4) + (1S,5R)-1-[(1,2-dihydroisoquinolin-2-yl)carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one (660861-32-5) → (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-[(1S)-1-phenyl-1,2-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-40-5)

Guidance literature:

(1S,5R)-1-[(1,2-dihydroisoquinolin-2-yl)carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one; With trityl tetrafluoroborate; In dichloromethane; at 20 ℃; for 16h;

phenylmagnesium chloride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 2h;

DOI:10.3987/com-03-s40

Reference yield:

diphenylzinc (1078-58-6) + (1S,5R)-1-[(1,2-dihydroisoquinolin-2-yl)carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one (660861-32-5) → (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-[(1S)-1-phenyl-1,2-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-40-5)

Guidance literature:

(1S,5R)-1-[(1,2-dihydroisoquinolin-2-yl)carbonyl]-5,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-2-one; With trityl tetrafluoroborate; In dichloromethane; at 20 ℃; for 16h;

diphenylzinc; In tetrahydrofuran; dichloromethane; at -90 ℃;

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-dihydroisoquinolin-2-ylcarbonyl]-3-oxabicyclo[3.2.1]octan-2-one (660861-45-0)

Guidance literature:

Multi-step reaction with 2 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

With tri-n-butyl-tin hydride; trityl tetrafluoroborate; In dichloromethane;

DOI:10.3987/com-03-s40

upstream raw materials:

phenylmagnesium chloride

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

diphenylzinc

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

Downstream raw materials:

(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