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

HRID 1727989Notes

Reaction equation

HRID 1727989 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].[CH3:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:27]=1[CH:33]=[N:34][C:35]([O:37][Si](C)(C)C)=[CH2:36]>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)[CH2:36][C:35](=[O:37])[NH:34][CH:33]2[C:27]2[C:28]([CH3:32])=[CH:29][CH:30]=[CH:31][C:26]=2[CH3:25])[C:7]1=[O:24])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 695137391-(2,6-Dimethylphenyl)-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 76568054racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-(2,6-dimethylphenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl esterYield 71%

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 (0.4 g, 1.08 mmol) prepared in example 4b was reacted with 1-(2,6-dimethylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (2.9 g, 11.7 mmol) prepared in example 27a, in toluene to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(2,6-dimethylphenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester (Yield 0.41 g, 71%).

Sources & evidence

ORD record
ord-34c293fdf2e845a3bde93f919ea89329
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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