1-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadiene → racemic (2'R,3R,4'S)-6-chloro-4'-(5-chloro-2-isopropoxy-phenyl)-2'-isopropenylspiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728166Notes

Reaction equation

HRID 1728166 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)/[C:10](=[CH:18]/[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][CH:27]([CH3:29])[CH3:28])/[C:9]1=[O:30])=O)(C)(C)C.[CH3:31][C:32]([CH:34]=[N:35][C:36]([O:38][Si](C)(C)C)=[CH2:37])=[CH2:33]>C1(C)C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[C:16]2[NH:8][C:9](=[O:30])[C:10]3([CH:18]([C:19]4[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=4[O:26][CH:27]([CH3:29])[CH3:28])[CH2:37][C:36](=[O:38])[NH:35][CH:34]3[C:32]([CH3:33])=[CH2:31])[C:11]2=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 765681151-Isopropenyl-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86617596Z-6-chloro-3-(5-chloro-2-isopropoxy-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 76568147racemic (2'R,3R,4'S)-6-chloro-4'-(5-chloro-2-isopropoxy-phenyl)-2'-isopropenylspiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 63.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in Example 41b, E/Z-6-Chloro-3-(5-chloro-2-isopropoxy-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (2 g, 4.47 mmol) was reacted with 1-(1-methyl-ethenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (22.37 mmol) in toluene to give title compound as a white solid (1.3 g).

Sources & evidence

ORD record
ord-db31ff1a93d94c90bd66676d51e4949c
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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