HCID 74370458, compound → HCID 68614563, compound

HRID 1728020Notes

Reaction equation

HRID 1728020 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:29])[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]([CH2:27][CH3:28])=[CH:25][CH3:26])[C:5]2=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pt]=O>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:29])[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[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 74370458HCID 74370458, compound

Product 1

HCID 68614563HCID 68614563, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-ethyl-propenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.3 g, 0.70 mmol) prepared in example 66b in ethyl acetate (30 mL) was added platinum oxide (0.35 g, 1.54 mmol). The resulting suspension was vigorously shaken under hydrogen (50 psi) for 6 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated. The residue was purified by chromatography (EtOAc:CH2Cl2=1:1) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-ethyl-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.11 g, 37.7%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by chromatography (EtOAc:CH2Cl2=1:1)

Sources & evidence

ORD record
ord-20b47644cfac4c87ac4fe6b536a0cece
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…