HCID 74370617, compound → HCID 86615090, compound

HRID 1728025Notes

Reaction equation

HRID 1728025 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]3[CH2:28][CH2:27][CH2:26][CH:25]=3)[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]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 74370617HCID 74370617, compound

Product 1

HCID 86615090HCID 86615090, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a manner similar to the method described in example 72, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(cyclopent-1-enyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.1 g, 0.23 mmol) prepared in example 77c was treated with platinum oxide in ethyl acetate under hydrogen (50 psi) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-cyclopentylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (0.031 g, 31%).

Sources & evidence

ORD record
ord-4558cce08c744f63bb099888e64804f9
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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