1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one

Base Information

• Chemical Name: 1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one
• CAS No.: 487003-06-5
• Molecular Formula: C₂₄H₂₁NO₂
• Molecular Weight: 355.436
• Mol file: 487003-06-5.mol

Synonyms:1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one

Chemical Property of 1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one

There total 1 articles about 1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one 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: 87.0%

1-benzyl-6-hydroxy-3,3-spirocyclopropyl-1,3-dihydroindol-2-one (487003-29-2) + benzyl bromide (100-39-0) → 1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one (487003-06-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1002/chem.200600957

Reference yield:

1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one (487003-06-5) + (3S,4R)-4-Allyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-1,2,3,4-tetrahydro-pyridine → (1'R*,6'R*,7'R*,8'aS*)-7'-allyl-1-benzyl-6'-(tert-butyldiphenylsilyloxymethyl)-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one

Guidance literature:

With magnesium iodide; In tetrahydrofuran; at 80 ℃; for 16h;

DOI:10.1021/ja027906k DOI:10.1002/chem.200600957

Reference yield:

1-benzyl-6-(phenylmethoxy)-3,3-spirocyclopropyl-1,3-dihydroindol-2-one (487003-06-5) → (1'R*,6'R*,7'R*,8'aS*)-1-benzyl-7'-(2,2-dimethoxyethyl)-6'-formyl-2',3',6',7',8',8'a-hexahydro-6-phenylmethoxy-spiro[3H-indole-3,1'(5'H)-indolizin]-2(1H)-one

Guidance literature:

Multi-step reaction with 6 steps

1: 588 mg / MgI₂ / tetrahydrofuran / 16 h / 80 °C

2: NMO; OsO₄ / H₂O; 2-methyl-propan-2-ol; dioxane / 4 h / 23 °C

3: 172 mg / NaIO₄ / H₂O; 2-methyl-propan-2-ol; dioxane / 2 h / 23 °C

4: 93 percent / p-TsOH / methanol / 12 h / 23 °C

5: 86 percent / TBAF / tetrahydrofuran / 5 h / 23 °C

6: 88 percent / IBX / dimethylsulfoxide / 12 h / 23 °C

With sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; magnesium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; water; dimethyl sulfoxide; tert-butyl alcohol;

DOI:10.1002/chem.200600957

upstream raw materials:

1-benzyl-6-hydroxy-3,3-spirocyclopropyl-1,3-dihydroindol-2-one

benzyl bromide