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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1727977Generated: November 2, 2026

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

https://huagongshe.com/reaction/1727977

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(2-Chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 76568087—
ReactantZ-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl esterHCID 86615084—
SolventTolueneHCID 1140—
Productracemic (2'R,3R,4'S)-6-chloro-2'-(2-chlorophenyl)-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl esterHCID 9078573167.1%

Reaction Steps

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 (0.31 g, 0.85 mmol) prepared in example 4b was reacted with 1-(2-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (2.1 g, 8.27 mmol) prepared in example 16a, in toluene to give racemic (2′R,3R,4′S)-6-chloro-2′-(2-chlorophenyl)-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester as a yellow gum (Yield 0.31 g, 67%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07495007B2
Source datasetuspto-grants-2009_02
ORD IDord-5028e91241cb452aa71d62cea19c51d5
Source noteuspto-grants-2009_02