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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1728026Generated: October 31, 2026

1-(1-Ethyl-propenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene → 6-Chloro-4'-(3-chloro-phenyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

https://huagongshe.com/reaction/1728026

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(1-Ethyl-propenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 76567890—
ReactantZ-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-oneHCID 86615089—
SolventTolueneHCID 1140—
Product6-Chloro-4'-(3-chloro-phenyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilaneHCID 7758007185%

Reaction Steps

In a manner similar to the method described in example 55b, E/Z-6-chloro-3-(3-chloro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indole-2-one (5.4 g, 12.8 mmol) prepared in example 55a was reacted with 1-(1-ethyl-propenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (20 g, 95 mmol) prepared in example 66a in toluene (200 mL) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-2′-(1-ethyl-propenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white gum (Yield 6.1 g, 85%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07495007B2
Source datasetuspto-grants-2009_02
ORD IDord-6bb496b58c3c4002ba0b293faf312799
Source noteuspto-grants-2009_02