(2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]

Base Information

• Chemical Name: (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]
• CAS No.: 1455213-48-5
• Molecular Formula: C₄₀H₃₁BrN₂O₆S
• Molecular Weight: 747.666
• Mol file: 1455213-48-5.mol

Synonyms:

Chemical Property of (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]

There total 4 articles about (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline] 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:

1-acetyl-3-(2-oxo-2-phenylethylidene)indolin-2-one (27312-31-8) + C22H18BrNO3S → (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline] (1455213-48-5) + (2’S,3’R,4’R)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]

Guidance literature:

1-acetyl-3-(2-oxo-2-phenylethylidene)indolin-2-one; With C₃₂H₂₈F₆N₄O₃; In dichloromethane; at 20 ℃; for 0.166667h;

C₂₂H₁₈BrNO₃S; In dichloromethane; Overall yield = 99 %; Overall yield = 74.2 mg; enantioselective reaction;

DOI:10.1039/c3cc44930k

Reference yield:

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) → (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline] (1455213-48-5) + (2’S,3’R,4’R)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / Reflux

2: toluene / 90 °C

3: C₃₂H₂₈F₆N₄O₃ / dichloromethane / 0.17 h / 20 °C

With dmap; C₃₂H₂₈F₆N₄O₃; In dichloromethane; toluene; 3: |Michael Addition;

DOI:10.1039/c3cc44930k

Reference yield:

para-bromoacetophenone (99-90-1) → (2’R,3’S,4’S)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline] (1455213-48-5) + (2’S,3’R,4’R)-1-acetyl-2’-benzoyl-4’-(2-oxo-1-(4-bromophenylethyl))-2-oxo-1’-tosylspiro[indoline-3,3’-tetrahydroquinoline]

Guidance literature:

Multi-step reaction with 4 steps

1: zirconium(IV) chloride / 1,2-dichloro-benzene / 60 °C

2: acetic acid; iron / ethanol / 70 °C

3: pyridine / Reflux

4: C₃₂H₂₈F₆N₄O₃ / dichloromethane / 0.17 h / 20 °C

With C₃₂H₂₈F₆N₄O₃; zirconium(IV) chloride; iron; acetic acid; In pyridine; ethanol; dichloromethane; 1,2-dichloro-benzene; 4: |Michael Addition;

DOI:10.1039/c3cc44930k

upstream raw materials:

1-acetyl-3-(2-oxo-2-phenylethylidene)indolin-2-one

para-bromoacetophenone

C₁₅H₁₀BrNO₃

indole-2,3-dione