(S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole

Base Information

• Chemical Name: (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole
• CAS No.: 222533-54-2
• Molecular Formula: C₂₃H₂₆N₂O₄
• Molecular Weight: 394.47
• Mol file: 222533-54-2.mol

Synonyms:(S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole

Chemical Property of (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole

There total 7 articles about (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole 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:

5-methoxyindolin-2-one (7699-18-5) → (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole (222533-54-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 -> -30 deg C, 2 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C

4: 95 percent / HCl / methanol

5: 97 percent / NaBH₄ / dioxane; methanol / 1 h

6: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; sodium hydride; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo981577q

Reference yield:

5-hydroxyoxindole (3416-18-0) → (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole (222533-54-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / potassium hydroxide / H₂O / 2 h

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 -> -30 deg C, 2 h

3: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C

5: 95 percent / HCl / methanol

6: 97 percent / NaBH₄ / dioxane; methanol / 1 h

7: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; sodium hydride; In 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1021/jo981577q

Reference yield:

5-methoxy-3-(3-methylbut-2-enyl)-2-oxindole (222533-48-4) → (S)-1-benzyl-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole (222533-54-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C

3: 95 percent / HCl / methanol

4: 97 percent / NaBH₄ / dioxane; methanol / 1 h

5: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h

With 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; sodium hydride; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jo981577q

upstream raw materials:

benzyl chloride

(S)-3-(3-methylbut-2-enyl)-5-methoxy-3-(2-nitroethyl)-2-oxindole

5-hydroxyoxindole

5-methoxyindolin-2-one

Downstream raw materials:

(R)-1-benzyl-3-(3-methylbut-2-enyl)-3-(benzyloxycarbonylaminomethyl)-5-methoxy-2-oxindole

(R)-1-benzyl-3-(2-hydroxyethyl)-3-(benzyloxycarbonylaminomethyl)-5-methoxy-2-oxindole

(R)-1-benzyl-1'-benzyloxycarbonyl-5-methoxy-2-oxospiro(3H-indole-3,3'-pyrrolidine)

(R)-1-benzyl-3-(3-methylbut-2-enyl)-3-(ethoxycarbonylaminomethyl)-5-methoxy-2-oxindole

Refernces