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

HRID 1727982Notes

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

Participants

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 90783015racemic (2'R,3R,4'S)-2'-(2-bromophenyl)-6-chloro-4'-(3-chlorophenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid ethyl ester

Product 1

HCID 131727316racemic (2'R,3R,4'S)-2'-(2-bromophenyl)-6-chloro-4'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 64%

Procedure

In a manner similar to the method described in example 4d, racemic (2′S,3R,4′S)-2′-(2-bromophenyl)-6-chloro-4′-(3-chlorophenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid ethyl ester (0.45 g, 0.76 mmol) was reacted with NaOH in methanol (2N, 5 mL, 10 mmol) to give racemic (2′R,3R,4′S)-2′-(2-bromophenyl)-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.25 g, 64%).

Sources & evidence

ORD record: ord-1a16bb3a78724d068c55e37cf24d0a74
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

Loading…