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

HRID 1727963Notes

Reaction equation

HRID 1727963 reaction equation
C(OC([N:6]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([Cl:34])[CH:32]=2)[C:8]2([CH:13]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][C:11](=[O:20])[NH:10][CH:9]2[C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:7]1=[O:35])=O)C.[OH-].[Na+]>CO>[Cl:34][C:31]1[CH:32]=[C:33]2[NH:6][C:7](=[O:35])[C:8]3([CH:13]([CH:14]4[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]4)[CH2:12][C:11](=[O:20])[NH:10][CH:9]3[C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)[C:28]2=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90768930racemic (2'S,3S,4'R)-6-chloro-2'-(4-chlorophenyl)-4'-cyclohexyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

Product 1

HCID 131727309racemic (2'S,3S,4'R)-6-chloro-2'-(4-chlorophenyl)-4'-cyclohexyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in example 4d, racemic (2′S,3S,4′R)-6-chloro-2′-(4-chlorophenyl)-4′-cyclohexyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester (0.4 g, 0.78 mmol) was reacted with NaOH (56 mg, 1.4 mmol) in methanol to give racemic (2′S,3S,4′R)-6-chloro-2′-(4-chlorophenyl)-4′-cyclohexylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.15 g, 44%).

Sources & evidence

ORD record
ord-33eebc95a18249988c40d4c73da04939
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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