(-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide

Base Information

• Chemical Name: (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide
• CAS No.: 446063-58-7
• Molecular Formula: C₂₄H₃₁NO₅S
• Molecular Weight: 445.58

Synonyms:(-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide

Chemical Property of (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide

Chemical Property:

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Technology Process of (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide

There total 3 articles about (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide 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: 84.0%

(-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]succinimide (446063-57-6) → (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide (446063-58-7)

Guidance literature:

With N-chloro-succinimide; In tetrachloromethane; for 16h; Heating;

DOI:10.1055/s-2002-22703 DOI:10.1021/jo049672o

Reference yield:

1‐(3,4‐dimethoxyphenethyl)‐1H‐pyrrole‐2,5‐dione (37597-19-6) → (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide (446063-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 84 percent / NCS / CCl₄ / 16 h / Heating

With N-chloro-succinimide; triethylamine; In tetrachloromethane; dichloromethane;

DOI:10.1021/jo049672o

Reference yield:

(1S,2R,4R)-(-)-10-mercaptoisoboneol (71242-58-5) → (-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]maleimide (446063-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 84 percent / NCS / CCl₄ / 16 h / Heating

With N-chloro-succinimide; triethylamine; In tetrachloromethane; dichloromethane;

DOI:10.1021/jo049672o

upstream raw materials:

(-)-[(1S,2R,4R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]-1-yl)methylsulfanyl]-N-[2-(3,4-dimethoxyphenyl)ethyl]succinimide

1‐(3,4‐dimethoxyphenethyl)‐1H‐pyrrole‐2,5‐dione

(1S,2R,4R)-(-)-10-mercaptoisoboneol

Downstream raw materials:

1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-pyrrole-2,5-dione

(2R,6S)-(-)-2-[(1S,2R,4R,S_R)-(2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methylsulfinyl]-4-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

(1R,2R,6S,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-5-hydroxy-2-((R)-(1S,2R,4R)-2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

(1R,2S,6R,7S)-4-[2-(3,4-Dimethoxy-phenyl)-ethyl]-5-methylene-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

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