Sodium Hydroxide → racemic (2'R,3R,4'S)-6-chloro-2',4'-bis(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'-dione

HRID 1727953Notes

Reaction equation

HRID 1727953 reaction equation
C(OC([N:6]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([Cl:35])[CH:33]=2)[C:8]2([CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH2:12][C:11](=[O:21])[NH:10][CH:9]2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C:7]1=[O:36])=O)C.[OH-].[Na+]>CO>[Cl:35][C:32]1[CH:33]=[C:34]2[NH:6][C:7](=[O:36])[C:8]3([CH:13]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=4)[CH2:12][C:11](=[O:21])[NH:10][CH:9]3[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:29]2=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 91457502racemic (2'R,3R, 4'S)-6-chloro-2',4'-bis(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

Product 1

HCID 131727306racemic (2'R,3R,4'S)-6-chloro-2',4'-bis(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'-dioneYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of racemic (2′R,3R,4′S)-6-chloro-2′,4′-bis(3-chlorophenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester prepared in example 4c (0.45 g, 0.92 mmol) in methanol (30 mL) was added NaOH (66 mg, 1.65 mmol). The mixture was stirred at room temperature for 0.5 h. The solvent was removed and the residue was partitioned between ethyl acetate and aqueous HCl solution (1 N). The aqueous layer was extracted with ethyl acetate. The organic layers were combined and then concentrated. The residue was purified with chromatography (EtOAc:CH2Cl2=1:3) to give racemic (2′R,3R,4′S)-6-chloro-2′,4′-bis(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′-dione as a white solid (Yield 0.2 g, 51%).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and aqueous HCl solution (1 N)
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. concentrationconcentrated
  5. customThe residue was purified with chromatography (EtOAc:CH2Cl2=1:3)

Sources & evidence

ORD record
ord-ed15fb58d76e4229b7762f540125087c
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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