E-6-chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-one → racemic (2'SR,3S,4'R)-4'-(tert-butyl)-6-chloro-2'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1727950Notes

Reaction equation

HRID 1727950 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:12]\[C:13]([CH3:16])([CH3:15])[CH3:14])/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[N:25][C:26]([O:28][Si](C)(C)C)=[CH2:27])[CH:21]=[CH:22][CH:23]=1>C1(C)C=CC=CC=1>[C:13]([CH:12]1[CH2:27][C:26](=[O:28])[NH:25][CH:24]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[CH:19]=2)[C:6]21[C:5]1[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)[NH:8][C:7]2=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 57565943E-6-chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-oneHCID 68961886HCID 68961886, compound

Product 1

HCID 131727304racemic (2'SR,3S,4'R)-4'-(tert-butyl)-6-chloro-2'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to the method described in example 1c, E-6-chloro-3-(2,2-dimethyl-propylidene)-1,3-dihydro-indol-2-one (0.23 g, 1 mmol) was reacted with 1-(3-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (0.63 g, 2.5 mmol) prepared in example 1b, in toluene to give racemic (2′SR,3S,4′R)-4′-(tert-butyl)-6-chloro-2′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a mixture of two sets of diastereomers (Yield 0.21 g, 50%).

Sources & evidence

ORD record
ord-942f8a618ec1414496c7a5980dbd2c84
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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