Trifluoroacetic acid → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-isopropenyl-1'-hydroxycarbonylmethyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728053Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:35])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[CH:11]3[C:32]([CH3:34])=[CH2:33])[C:5]2=[CH:4][CH:3]=1.[CH3:36]OC([Si](C)(C)C)C.FC(F)(F)C(O)=O>>[CH2:24]([N:12]([CH:11]([CH3:10])[CH3:32])[CH:13]([CH3:14])[CH3:36])[CH3:25].[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:35])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][C:25]([OH:27])=[O:26])[CH:11]3[C:32]([CH3:34])=[CH2:33])[C:5]2=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 775802646-Chloro-4'-(3-chlorophenyl)-2'-isopropenyl-2,3-dihydro-1'-[(tert-butoxycarbonyl) methyl]-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane

Product 2

HCID 81531Diisopropylethylamine

HCID 76568119racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-isopropenyl-1'-hydroxycarbonylmethyl spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 166%

Procedure

In a manner similar to the method described in example 55d, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-isopropenyl-2,3-dihydro-1′-[(tert-butoxycarbonyl)methyl]-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (2.88 g, 4.46 mmol) prepared in example 116b was reacted with trifluoroacetic acid, then ethyl-diisopropyl-amine to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-isopropenyl-1′-hydroxycarbonylmethylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as yellow oil (Yield 1.7 g, 85.8%).

Sources & evidence

ORD record: ord-442a9fb0e323489cb263ea048b378b1e
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495007B2

Reaction notes

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