Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2'-(2-methylphenyl)-2,6'-dioxospiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

HRID 1727983Notes

Reaction equation

HRID 1727983 reaction equation
[C:1]([O:5][C:6]([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]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)/[C:9]1=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]=[N:35][C:36]([O:38][Si](C)(C)C)=[CH2:37]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]2([CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[CH2:37][C:36](=[O:38])[NH:35][CH:34]2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH3:27])[C:9]1=[O:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 66640668Z-6-chloro-3-(3-chloro-benzylidene)-2-oxo-2,3-dihydro-indole-1-carboxylic acid tert-butyl esterHCID 675412941-(2-Methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene

Product 1

HCID 90866629racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2'-(2-methylphenyl)-2,6'-dioxospiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl esterYield 65%

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 tert-butyl ester (1 g, 2.6 mmol) prepared in example 24a was reacted with 1-(2-methylphenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (3.3 g, 14.1 mmol) prepared in example 17a, in toluene to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester as a white foam (Yield: 0.92 g, 65%).

Sources & evidence

ORD record
ord-45da9f67ae464003bc831160b7829119
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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