(S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione

Base Information

• Chemical Name: (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione
• CAS No.: 891186-81-5
• Molecular Formula: C₂₂H₂₄N₂O₅
• Molecular Weight: 396.443
• Mol file: 891186-81-5.mol

Synonyms:(S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione

Chemical Property of (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione

There total 11 articles about (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione 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: 85.0%

N-(2,4-dimethoxybenzyl)-N-(2-iodo-4-methoxyphenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide → (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione (891186-81-5)

Guidance literature:

With copper(l) iodide; N,N'-Dimethylurea; sodium hydride; (S,S)-N,N'-dimethyl-1,2-diphenylethane-1,2-diamine; In acetonitrile; at 20 ℃; for 8h; enantioselective reaction;

DOI:10.1039/d1ob01327k

Reference yield: 66.0%

1-(2,4-dimethoxy-benzyl)-5-methoxy-2-oxo-3-(2-oxo-ethyl)-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester (891186-79-1) + methylamine (74-89-5) → (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione (891186-81-5) + 1-(2,4-dimethoxy-benzyl)-5'-hydroxy-5-methoxy-1'-methyl-1H-spiro[indole-3,3'-pyrrolidine]-2,2-dione

Guidance literature:

1-(2,4-dimethoxy-benzyl)-5-methoxy-2-oxo-3-(2-oxo-ethyl)-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester; methylamine; With magnesium sulfate; In tetrahydrofuran; at 20 ℃; for 1.5h;

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 0.5h;

DOI:10.1021/ol060298j

Reference yield:

1-(2,4-dimethoxy-benzyl)-5-methoxy-2-oxo-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester → (S)-1-(2,4-dimethoxybenzyl)-5-methoxy-1'-methylspiro[indoline-3,3'-pyrrolidine]-2,2'-dione (891186-81-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 15.47 g / triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

2.1: N,N'-(1R,2R)-cyclohexane-1,2-diylbis[2-(PPh₂)benzamide]; TBAT / [Pd(C₃H₅)Cl]2 / toluene / 12 h

3.1: N-methylmorpholine-N-oxide; osmium tetraoxide / H₂O; CH₂Cl₂ / 6 h / 20 °C

4.1: 1.35 g / lead tetraacetate / CH₂Cl₂ / 0.25 h

5.1: magnesium sulfate / tetrahydrofuran / 1.5 h / 20 °C

5.2: 66 percent / sodium borohydride / ethanol / 0.5 h / 20 °C

With lead(IV) acetate; osmium(VIII) oxide; magnesium sulfate; 4-methylmorpholine N-oxide; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; tetrabutylammonium triphenyldifluorosilicate; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/ol060298j

upstream raw materials:

1-(2,4-dimethoxy-benzyl)-5-methoxy-2-oxo-3-(2-oxo-ethyl)-2,3-dihydro-1H-indole-3-carboxylic acid ethyl ester

methylamine

ethyl 2-diazo-3-(N-(2,4-dimethoxybenzyl)-N-(4-methoxyphenyl)amino)-3-oxopropanoate

3-allyl-1-(2,4-dimethoxy-benzyl)-5-methoxy-2-oxo-2,3-dihydro-1-H-indole-3-carboxylic acid ethyl ester