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

HRID 1727969Notes

Reaction equation

HRID 1727969 reaction equation
C(OC([N:6]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([Cl:35])[CH:33]=2)[C:8]2([CH:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:12][C:11](=[O:21])[NH:10][CH:9]2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C:7]1=[O:36])=O)C.[OH-].[Na+]>CO>[Cl:35][C:32]1[CH:33]=[C:34]2[NH:6][C:7](=[O:36])[C:8]3([CH:13]([C:14]4[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=4)[CH2:12][C:11](=[O:21])[NH:10][CH:9]3[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:29]2=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76567914racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-(4-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

Product 1

HCID 131727311racemic (2'S,3S,4'R)-6-chloro-2'-(3-chlorophenyl)-4'-(4-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 18.4%

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′-(4-chlorophenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester (0.5 g, 0.92 mmol) was reacted with NaOH (67 mg, 1.67 mmol) in methanol to give racemic (2′S,3S,4′R)-6-chloro-2′-(3-chlorophenyl)-4′-(4-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.08 g, 18%).

Sources & evidence

ORD record
ord-58d2225ac3d647619f8dca6bfd006222
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

Loading…