1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione

Base Information

• Chemical Name: 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione
• CAS No.: 1610952-14-1
• Molecular Formula: C₂₃H₂₂BrF₂N₃O₅S
• Molecular Weight: 570.412
• Mol file: 1610952-14-1.mol

Synonyms:1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione

Chemical Property of 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione

There total 5 articles about 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione 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: 66.0%

3-Bromobenzenesulfonyl chloride (2905-24-0) + 10-[2-(difluoromethoxy)benzyl]-2'H,5'H-spiro-[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione (1610952-11-8) → 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione (1610952-14-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1002/ardp.201300289

Reference yield:

tert-butyl 1'-[2-(difluoromethoxy)benzyl]-2',5'-dioxo-8H-spiro[8-azabicycle[3.2.1]octane-3,4'-imidazolidine]-8-carboxylate (1610952-10-7) → 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione (1610952-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; water / 1,4-dioxane / 4 h / 0 - 20 °C

2: triethylamine / dichloromethane / 16 h / 20 °C

With hydrogenchloride; water; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1002/ardp.201300289

Reference yield:

(8-azabicyclo[3.2.1]octan-3-one) hydrochloride → 1'-[2-(difluoromethoxy)benzyl]-8-[(3-bromophenyl)sulfonyl]-2'H,5'H-spiro[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione (1610952-14-1)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 16 h / 20 °C

2: water; ethanol / 48 h / 20 - 50 °C

3: potassium carbonate / acetonitrile / 6 h / Reflux

4: hydrogenchloride; water / 1,4-dioxane / 4 h / 0 - 20 °C

5: triethylamine / dichloromethane / 16 h / 20 °C

With hydrogenchloride; water; potassium carbonate; triethylamine; In 1,4-dioxane; ethanol; dichloromethane; water; acetonitrile; 2: |Bucherer-Bergs Reaction;

DOI:10.1002/ardp.201300289

upstream raw materials:

tert-butyl 1'-[2-(difluoromethoxy)benzyl]-2',5'-dioxo-8H-spiro[8-azabicycle[3.2.1]octane-3,4'-imidazolidine]-8-carboxylate

3-Bromobenzenesulfonyl chloride

10-[2-(difluoromethoxy)benzyl]-2'H,5'H-spiro-[8-azabicyclo[3.2.1]octane-3,4'-imidazolidine]-2',5'-dione

N-Boc-nortropinone