HCID 68961886, compound → racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-cyclopentyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

HRID 1727956Notes

Reaction equation

HRID 1727956 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[CH2:21][CH2:20][CH2:19][CH2:18]2)/[C:7]1=[O:22])=[O:5])[CH3:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[N:31][C:32]([O:34][Si](C)(C)C)=[CH2:33])[CH:27]=[CH:28][CH:29]=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]3)[CH2:33][C:32](=[O:34])[NH:31][CH:30]2[C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([Cl:23])[CH:25]=2)[C:7]1=[O:22])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 68961886HCID 68961886, compoundHCID 86615085Z-6-chloro-3-cyclopentylmethylene-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester

Product 1

HCID 90971499racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-cyclopentyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 4c, E/Z-6-chloro-3-cyclopentylmethylene-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester (0.32 g, 1.00 mmol) was reacted with 1-(3-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene prepared in example 1b, in toluene to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-cyclopentyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester as an off-white foam (Yield 0.26 g, 52%).

Sources & evidence

ORD record
ord-651240602c72458c82351c8142cc411e
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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