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

Base Information

• Chemical Name: (2′S,3′R)-tert-butyl 1-methyl-2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate
• CAS No.: 1403337-94-9
• Molecular Formula: C₂₃H₂₄N₂O₄
• Molecular Weight: 392.455
• Mol file: 1403337-94-9.mol

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

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

There total 6 articles about (2′S,3′R)-tert-butyl 1-methyl-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: 83.0%

tert-butyl 1-methyl-2-oxoindolin-3-ylidenecarbamate (1373942-83-6) + 3-phenyl-propenal (104-55-2) → (2′S,3′R)-tert-butyl 1-methyl-2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate (1403337-94-9)

Guidance literature:

With C₂₂H₂₃N₂O⁽¹⁺⁾*BF₄^(1-); caesium carbonate; In tetrahydrofuran; at 20 ℃; for 24h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/ol302475g DOI:10.1021/ol302475g

Reference yield: 67.0%

tert-butyl 1-methyl-2-oxoindolin-3-ylidenecarbamate (1373942-83-6) + 3-phenyl-propenal (104-55-2) → (2′S,3′R)-tert-butyl 1-methyl-2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate (1403337-94-9) + (R,E)-tert-butyl (3-cinnamoyl-1-methyl-2-oxoindolin-3-yl)carbamate (1612251-15-6)

Guidance literature:

With BF₄^(1-)*C₁₈H₁₃Cl₃N₃O⁽¹⁺⁾; potassium acetate; In chloroform; at 20 ℃; Schlenk technique; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol501286e

Reference yield: 51.0%

(1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)-carbamic acid tert-butyl ester + α-bromocinnamaldehyde (5443-49-2) → (2′S,3′R)-tert-butyl 1-methyl-2,5′-dioxo-3′-phenylspiro[indoline-3,2′-pyrrolidine]-1′-carboxylate (1403337-94-9)

Guidance literature:

With (R)-5-benzyl-2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 45 ℃; for 10h; Reagent/catalyst; Solvent; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.joc.5b02188

upstream raw materials:

tert-butyl 1-methyl-2-oxoindolin-3-ylidenecarbamate

3-phenyl-propenal

α-bromocinnamaldehyde

Downstream raw materials:

C₁₈H₁₆N₂O₂