(3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione

Base Information

• Chemical Name: (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione
• CAS No.: 187157-80-8
• Molecular Formula: C₃₂H₂₇N₃O₃
• Molecular Weight: 501.585
• Mol file: 187157-80-8.mol

Synonyms:(3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione

Chemical Property of (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione

There total 10 articles about (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-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:

dimethyl (2S,3S)-2-azido-3-(9-phenyl-9H-fluoren-9-ylamino)succinate (159434-59-0) → (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione (187157-80-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) H₂, 2.) Na₂CO₃ / 1.) Pd/BaCO₃ / 1.) MeOH, 1 atm, 3 h, 2.) CH₂Cl₂, H₂O, reflux, 54 h

2: 83 percent / DMAP / pyridine / 0.33 h / 70 °C

3: 100 percent / MeLi, LiBr / tetrahydrofuran; diethyl ether / 1.25 h / -78 °C

4: DIBAL-H / CH₂Cl₂; hexane / 1.17 h / -78 °C

5: 90 percent / NaN₃ / dimethylformamide / 6.5 h / 110 °C

6: LiOH / dioxane; H₂O / 14 h / Ambient temperature

7: 1.) H₂, p-TsOH, 2.) DPPA, Et₃N / 1.) Pd/C / 1.) MeOH, 1 atm, 75 min, 2.) DMF, 0-20 deg C, 22 h

With dmap; lithium hydroxide; sodium azide; diphenyl-phosphinic acid; methyllithium; hydrogen; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid; triethylamine; lithium bromide; palladium on activated charcoal; palladium-barium carbonate; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970277q

Reference yield:

(2S,3S)-2-Benzylamino-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester (191406-43-6) → (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione (187157-80-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / DMAP / pyridine / 0.33 h / 70 °C

2: 100 percent / MeLi, LiBr / tetrahydrofuran; diethyl ether / 1.25 h / -78 °C

3: DIBAL-H / CH₂Cl₂; hexane / 1.17 h / -78 °C

4: 90 percent / NaN₃ / dimethylformamide / 6.5 h / 110 °C

5: LiOH / dioxane; H₂O / 14 h / Ambient temperature

6: 1.) H₂, p-TsOH, 2.) DPPA, Et₃N / 1.) Pd/C / 1.) MeOH, 1 atm, 75 min, 2.) DMF, 0-20 deg C, 22 h

With dmap; lithium hydroxide; sodium azide; diphenyl-phosphinic acid; methyllithium; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970277q

Reference yield:

(4S,5S)-1-benzyl-2-oxo-3-(9'-phenylfluoren-9'-yl)imidazolidine-4,5-dicarboxylic acid dimethyl ester (187157-73-9) → (3aS,7R,7aS)-1-Benzyl-7-hydroxy-3-(9-phenyl-9H-fluoren-9-yl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione (187157-80-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / MeLi, LiBr / tetrahydrofuran; diethyl ether / 1.25 h / -78 °C

2: DIBAL-H / CH₂Cl₂; hexane / 1.17 h / -78 °C

3: 90 percent / NaN₃ / dimethylformamide / 6.5 h / 110 °C

4: LiOH / dioxane; H₂O / 14 h / Ambient temperature

5: 1.) H₂, p-TsOH, 2.) DPPA, Et₃N / 1.) Pd/C / 1.) MeOH, 1 atm, 75 min, 2.) DMF, 0-20 deg C, 22 h

With lithium hydroxide; sodium azide; diphenyl-phosphinic acid; methyllithium; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo970277q

upstream raw materials:

(4S,5S)-5-((R)-2-Azido-1-hydroxy-ethyl)-1-benzyl-2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-imidazolidine-4-carboxylic acid

benzyl bromide

dimethyl (2S,3S)-2-azido-3-(9-phenyl-9H-fluoren-9-ylamino)succinate

(2S,3S)-2-Benzylamino-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester