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

HRID 1727962Notes

Reaction equation

HRID 1727962 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)/[C:8](=[CH:16]/[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)/[C:7]1=[O:23])=[O:5])[CH3:2].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]=[N:32][C:33]([O:35][Si](C)(C)C)=[CH2:34])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:15])[CH:13]=2)[C:8]2([CH:16]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:35][C:33](=[O:34])[NH:32][CH:31]2[C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=2)[C:7]1=[O:23])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 765680091-(4-Chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadieneHCID 86615086Z-6-chloro-3-cyclohexylmethylene-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

Product 1

HCID 90768930racemic (2'S,3S,4'R)-6-chloro-2'-(4-chlorophenyl)-4'-cyclohexyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 4c, E/Z-6-chloro-3-cyclohexylmethylene-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester (0.40 g, 1.20 mmol) prepared in example 6b was reacted with 1-(4-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 7a, in toluene to give racemic (2′S,3S,4′R)-6-chloro-2′-(4-chlorophenyl)-4′-cyclohexyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester as a white solid (Yield 0.45 g, 72%).

Sources & evidence

ORD record
ord-510edac56980428b98e23022648b2a2f
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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