Trifluoroacetic acid → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-methyl-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1727985Notes

Reaction equation

HRID 1727985 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([Cl:45])[CH:43]=2)[C:17]2([CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[CH2:21][C:20](=[O:30])[N:19]([CH3:31])[CH:18]2[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])[C:16]1=[O:46])=O)(C)(C)C>ClCCl>[Cl:45][C:42]1[CH:43]=[C:44]2[NH:15][C:16](=[O:46])[C:17]3([CH:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)[CH2:21][C:20](=[O:30])[N:19]([CH3:31])[CH:18]3[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])[C:39]2=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90718123racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-1'-methyl-2'-(2-methylphenyl)-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

Product 1

HCID 131727317racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-methyl-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-1′-methyl-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (0.20 g, 0.35 mmol) prepared in example 24c in dichloromethane (10 mL). The mixture was stirred at room temperature for 1 h. The solvent was evaporated in vacuo. To this residue was added saturated NaHCO3 solution, and extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried over MgSO4. The solvent was removed and the residue was purified by chromatography (EtOAc:CH2Cl2=1:4) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-methyl-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield: 0.075 g, 46%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionTo this residue was added saturated NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed
  7. customthe residue was purified by chromatography (EtOAc:CH2Cl2=1:4)

Sources & evidence

ORD record
ord-53bd87c49b8b46d28b87ebcd777be75f
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…