1-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadiene → 6-Chloro-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

HRID 1728051Notes

Reaction equation

HRID 1728051 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:20]/[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)/[C:7](=[O:19])[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si](C)(C)C)=[CH:4][CH:3]=1.[C:28]([CH:31]=[N:32][C:33]([O:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[CH2:34])([CH3:30])=[CH2:29]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:19])[C:6]3([CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[CH2:34][C:33](=[O:35])[NH:32][CH:31]3[C:28]([CH3:30])=[CH2:29])[C:5]2=[CH:4][CH:3]=1.[CH3:11][O:12][CH:13]([Si:36]([CH3:37])([CH3:38])[CH3:39])[CH3:14]

Participants

4

Reactant 2

HCID 765681151-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615089Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one

Product 1

HCID 775803116-Chloro-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 55b, E/Z-6-chloro-3-(3-chlorobenzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one (8 g, 20 mmol) prepared in example 55a was reacted with 1-isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadiene (21 g, 99 mmol) prepared in example 87a in toluene (200 mL) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-isopropenyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white gum (3.5 g, 33%)

Sources & evidence

ORD record
ord-a0b8ef070a364832a488c9a7d1815354
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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