(5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

Base Information

• Chemical Name: (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione
• CAS No.: 1373247-37-0
• Molecular Formula: C₁₄H₁₃Br₂NO₄
• Molecular Weight: 419.07
• Mol file: 1373247-37-0.mol

Synonyms:(5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

Chemical Property of (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

There total 8 articles about (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-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: 84.0%

(5S,9R)-9-(3-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione (1373247-35-8) → (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione (1373247-37-0)

Guidance literature:

With formic acid; bromine; zinc(II) chloride; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201109221

Reference yield:

(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate (1373247-33-6) → (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione (1373247-37-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C / 760.05 Torr

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere

2.2: 0.17 h / 20 °C

3.1: 1,4-dioxane / 0.17 h / 100 °C / Inert atmosphere

3.2: 2 h / Reflux

4.1: formic acid; bromine; zinc(II) chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With formic acid; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; bromine; N,N-dimethyl-formamide; zinc(II) chloride; In 1,4-dioxane; methanol; dichloromethane; 3.1: Curtius rearrangement;

DOI:10.1002/anie.201109221

Reference yield:

4-(3-methoxyphenyl)furan-2(5H)-one (7706-85-6) → (5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione (1373247-37-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (S)-(+)-4,4'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-3,3'-bi(1,2-methylenedioxybenzene); copper(l) chloride; sodium t-butanolate; tert-butyl alcohol / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 70 °C / Inert atmosphere

4.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C / 760.05 Torr

5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere

5.2: 0.17 h / 20 °C

6.1: 1,4-dioxane / 0.17 h / 100 °C / Inert atmosphere

6.2: 2 h / Reflux

7.1: formic acid; bromine; zinc(II) chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With (S)-(+)-4,4'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-3,3'-bi(1,2-methylenedioxybenzene); formic acid; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; bromine; potassium carbonate; N,N-dimethyl-formamide; copper(l) chloride; zinc(II) chloride; lithium hexamethyldisilazane; sodium t-butanolate; tert-butyl alcohol; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Michael addition / 6.1: Curtius rearrangement;

DOI:10.1002/anie.201109221

upstream raw materials:

(3S,4R)-benzyl 3-(3-methoxy-3-oxopropyl)-4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

(5S,9R)-9-(3-methoxyphenyl)-7-oxa-1-azaspiro[4.4]nonane-2,6-dione

(3R,4S)-benzyl 4-(3-methoxyphenyl)-2-oxotetrahydrofuran-3-carboxylate

4-(3-methoxyphenyl)furan-2(5H)-one

Downstream raw materials:

C₁₅H₁₆Br₂N₂O₄

(5S,9R)-9-(2,4-dibromo-5-methoxyphenyl)-7-methyl-1,7-diazaspiro[4.4]nonane-2,6,8-trione