Ozone → HCID 76568170, compound

HRID 1728042Notes

Reaction equation

HRID 1728042 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24](=C)[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.[O:29]=[O+][O-]>CO.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24](=[O:29])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24823OzoneHCID 775802116-chloro-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 76568170HCID 76568170, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (300 mg, 0.72 mmol) prepared in example 80b in methanol and dichloromethane (1:1, 50 mL) at −78° C. was passed a stream of ozone until the color of the solution turned blue. The reaction mixture was degassed with nitrogen, then methyl disulfide (5 mL) was added. The reaction was slowly warmed to room temperature and stirred overnight. The mixture was concentrated, and the residue was purified by chromatography (EtOAc:CH2Cl2=1:1) to give the racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-propionylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 160 mg, 50%)

Workup

  1. customat −78° C.
  2. customThe reaction mixture was degassed with nitrogen
  3. additionmethyl disulfide (5 mL) was added
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by chromatography (EtOAc:CH2Cl2=1:1)

Sources & evidence

ORD record
ord-3b9ea53be4ea454f9c7753a7ff5439b7
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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