1-(4-Chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → racemic (2'R,3R,4'S)-6-chloro-2'-(4-chlorophenyl)-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

HRID 1727964Notes

Reaction equation

HRID 1727964 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)/[C:8](=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)/[C:7]1=[O:24])=[O:5])[CH3:2].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]=[N:33][C:34]([O:36][Si](C)(C)C)=[CH2:35])=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[C:8]2([CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH2:35][C:34](=[O:36])[NH:33][CH:32]2[C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=2)[C:7]1=[O:24])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 765680091-(4-Chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615084Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

Product 1

HCID 90943590racemic (2'R,3R,4'S)-6-chloro-2'-(4-chlorophenyl)-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 4c, E/Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester (0.3 g, 0.83 mmol) prepared in example 4b was reacted with 1-(4-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 7a, in toluene to give racemic (2′R,3R,4′S)-6-chloro-2′-(4-chlorophenyl)-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester as a yellow solid (Yield 0.45 g, 72%).

Sources & evidence

ORD record
ord-2c6b7a761601455ea25f3f004d91608c
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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