Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 5-methoxy-1'-methyl-

Base Information

• Chemical Name: Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 5-methoxy-1'-methyl-
• CAS No.: 136316-07-9
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.282
• Mol file: 136316-07-9.mol

Synonyms:

Chemical Property of Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 5-methoxy-1'-methyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 5-methoxy-1'-methyl-

There total 2 articles about Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-one, 5-methoxy-1'-methyl- 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: 57.0%

5-methoxyindolin-2-one (7699-18-5) + 3’-methyl-10H-spiro[anthracene-9,5’-oxazolidin]-10-one → horsfiline (136316-07-9)

Guidance literature:

5-methoxyindolin-2-one; 3’-methyl-10H-spiro[anthracene-9,5’-oxazolidin]-10-one; In o-xylene; at 225 ℃; for 0.75h; Microwave irradiation; Sealed tube; Inert atmosphere;

With hydrogenchloride; In methanol; water; for 1.5h; Reflux;

DOI:10.1021/acs.joc.7b02193

Reference yield:

5-methoxyindolin-2-one (7699-18-5) → horsfiline (136316-07-9)

Guidance literature:

Multi-step reaction with 14 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

7: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C

8: 71 percent / triethylamine, diphenylphosphoryl azide / 48 h / Heating

9: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, room temperature, overnight

10: 50 mg / NaBH₄ / methanol / 1 h

11: triethylamine / CH₂Cl₂ / 1 h / 0 °C

12: 32 mg / NaH / tetrahydrofuran; paraffin / 10 h / Ambient temperature

13: 1.) potassium hydroxide, hydrazine, 2.) formic acid / 1.) ethylene glycol, 100 deg C, 10 h, 2.) water, reflux, 1 h

14: lithium, liq. ammonia

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; formic acid; dimethylsulfide; diphenylphosphoranyl azide; ammonia; lithium; sodium hydride; ozone; acetic acid; triethylamine; hydrazine; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; paraffin;

DOI:10.1021/jo981577q

upstream raw materials:

5-methoxyindolin-2-one

Refernces

• 1、 Lakshmaiah, Gingipalli,Kawabata, Takeo,Shang, Muhong,Fuji, Kaoru. "Total Synthesis of (-)-horsfiline via asymmetric nitroolefination". . p. 1699 - 1704. Retrieved 2007/10/03.