Toluene → 6-chloro-2'-(3-chlorophenyl)-4'-(2,2-dimethylpropyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[N:9][C:10]([O:12][Si](C)(C)C)=[CH2:11])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC=CC=1.[Cl:24][C:25]1[CH:33]=[C:32]2[C:28](/[C:29](=[CH:35]/[CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])/[C:30](=[O:34])[NH:31]2)=[CH:27][CH:26]=1>CO>[Cl:24][C:25]1[CH:33]=[C:32]2[NH:31][C:30](=[O:34])[C:29]3([CH:35]([CH2:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH2:12][C:10](=[O:11])[NH:9][CH:8]3[C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:28]2=[CH:27][CH:26]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a mixture of 1-(3-chlorophenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (0.25 g, 1 mmol) prepared in example 1b, and toluene (4 mL) was added E/Z-6-chloro-3-(3,3-dimethyl-butylidene)-1,3-dihydro-indol-2-one (0.25 g, 1 mmol) prepared in example 1a. The reaction mixture was heated in a sealed tube under nitrogen at 110° C. for 18 h. The mixture was cooled to room temperature, and methanol (10 mL) was added. The mixture was concentrated and the residue was purified by chromatography (EtOAc/hexanes=2:1) to give racemic (2′S,3S,4′S)-6-chloro-2′-(3-chlorophenyl)-4′-(2,2-dimethylpropyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a brown solid (Yield 0.15 g, 35%).
Workup
- temperatureThe mixture was cooled to room temperature
- concentrationThe mixture was concentrated
- customthe residue was purified by chromatography (EtOAc/hexanes=2:1)
Sources & evidence
- ORD record
- ord-42cb710dd80d44b18fa28974a4bfe4e0
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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