(2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

Base Information

Chemical Name:(2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate
CAS No.:1286738-59-7
Molecular Formula:C₂₅H₂₁ClN₂O₃
Molecular Weight:432.906
Hs Code.:

Synonyms:(2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

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Chemical Property of (2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

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Technology Process of (2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

There total 4 articles about (2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-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: 70.0%

: 3359-49-7,23772-61-4,23782-37-8
3-benzylideneoxindole

: 135998-78-6
methyl [(2-chlorobenzylidene)amino]acetate

: 1286738-59-7
(2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

Guidance literature:: With (S)-TF-BiphamPhos; silver(I) acetate; triethylamine; In dichloromethane; at 20 ℃; for 1h; stereoselective reaction; Inert atmosphere;
DOI:10.1002/chir.22746

Reference yield:

: 3359-49-7,23772-61-4,23782-37-8
3-benzylideneoxindole

: 135998-78-6
methyl [(2-chlorobenzylidene)amino]acetate

: 1286738-59-7
(2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

: (2'S,3R,4'S,5'S)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

Guidance literature:: With (S)-TF-BiphamPhos; silver(I) acetate; triethylamine; In dichloromethane; at 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1039/c0ob00943a

Reference yield:

: 91-56-5,1186480-61-4,84788-92-1
indole-2,3-dione

: 1286738-59-7
(2'R,3S,4'R,5'R)-methyl 2'-(2-chlorophenyl)-2-oxo-4'-phenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrazine hydrate / ethanol / 3 h / Reflux

1.2: 0.5 h / 0 °C / Reflux

2.1: piperidine / ethanol / Reflux

3.1: triethylamine; (S)-TF-BiphamPhos; silver(I) acetate / dichloromethane / 1 h / 20 °C / Inert atmosphere

With piperidine; (S)-TF-BiphamPhos; silver(I) acetate; hydrazine hydrate; triethylamine; In ethanol; dichloromethane;
DOI:10.1002/chir.22746