(2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate

Base Information

• Chemical Name: (2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate
• CAS No.: 1403337-97-2
• Molecular Formula: C₂₂H₂₂N₂O₄
• Molecular Weight: 378.428
• Mol file: 1403337-97-2.mol

Synonyms:(2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate

Chemical Property of (2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate

There total 2 articles about (2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate 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:

tert-butyl 2-oxoindolin-3-ylidenecarbamate (1373942-82-5) + 3-phenyl-propenal (104-55-2) → (2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate (1403337-97-2) + tert-butyl 2,5'-dioxo-3'-phenylspiro[indoline-3,2'-pyrrolidine]-1'-carboxylate

Guidance literature:

With C₂₂H₂₃N₂O⁽¹⁺⁾*BF₄^(1-); caesium carbonate; In tetrahydrofuran; at 40 ℃; for 24h; Overall yield = 64 %; Overall yield = 48.4 mg; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol302475g DOI:10.1021/ol302475g

Reference yield:

α-bromocinnamaldehyde (5443-49-2) + 3-Boc-aminooxindole → (2′S,3′R)-tert-butyl 2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate (1403337-97-2) + C22H22N2O4

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate; caesium carbonate; In toluene; at 20 ℃; Overall yield = 52 %; Overall yield = 39.3 mg; stereoselective reaction; Schlenk technique;

DOI:10.1039/c5ob02466h

upstream raw materials:

tert-butyl 2-oxoindolin-3-ylidenecarbamate

3-phenyl-propenal

α-bromocinnamaldehyde