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

HRID 1727957Notes

Reaction equation

HRID 1727957 reaction equation
C(OC([N:6]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([Cl:33])[CH:31]=2)[C:8]2([CH:13]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][C:11](=[O:19])[NH:10][CH:9]2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[C:7]1=[O:34])=O)C.[OH-].[Na+]>CO>[Cl:33][C:30]1[CH:31]=[C:32]2[NH:6][C:7](=[O:34])[C:8]3([CH:13]([CH:14]4[CH2:18][CH2:17][CH2:16][CH2:15]4)[CH2:12][C:11](=[O:19])[NH:10][CH:9]3[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:27]2=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90971499racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-cyclopentyl-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

Product 1

HCID 131727307racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-cyclopentyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 59%

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′-(3-chlorophenyl)-4′-cyclopentyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester (0.26 g, 0.52 mmol) was reacted with NaOH (37 mg, 0.93 mmol) in methanol to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-cyclopentylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.13 g, 59%).

Sources & evidence

ORD record
ord-1d3525333c4744059cccc178a0480d1b
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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