Sodium Hydroxide → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-(2,6-dimethylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1727990Notes

Reaction equation

HRID 1727990 reaction equation
C(OC([N:6]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([Cl:36])[CH:34]=2)[C@@:8]2([C@H: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][C@@H:9]2[C:22]2[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:29])[C:7]1=[O:37])=O)C.[OH-].[Na+]>CO>[Cl:36][C:33]1[CH:34]=[C:35]2[NH:6][C:7](=[O:37])[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[C:23]([CH3:29])=[CH:24][CH:25]=[CH:26][C:27]=3[CH3:28])[C:30]2=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57566073(2'r,3r,4's)-6-Chloro-4'-(3-chlorophenyl)-2'-(2,6-dimethylphenyl)-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

Product 1

HCID 74371669racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-(2,6-dimethylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in example 4d, (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(2,6-dimethylphenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester (0.41 g, 0.76 mmol) was reacted with NaOH (0.4 g, 10 mmol) in methanol to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(2,6-dimethylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (Yield 0.25 g, 71%).

Sources & evidence

ORD record
ord-aa9f66113fe94d51ab7c5046b7926a72
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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