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

HRID 1727988Notes

Reaction equation

HRID 1727988 reaction equation
C(OC([N:8]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([Cl:39])[CH:37]=2)[C:10]2([CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[N:12]([CH2:24][CH3:25])[CH:11]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[C:9]1=[O:40])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:39][C:36]1[CH:37]=[C:38]2[NH:8][C:9](=[O:40])[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][CH3:25])[CH:11]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[C:33]2=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90883474racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-ethyl-2,3-dihydro-2'-(2-methylphenyl)-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

Product 1

HCID 131727319racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-ethyl-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to the method described in example 24d, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-ethyl-2,3-dihydro-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (0.2 g, 0.34 mmol) prepared in example 26a was reacted with trifluoroacetic acid in dichlormethane to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-ethyl-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as an off-white foam (Yield: 0.11 g, 69%).

Sources & evidence

ORD record
ord-dffd5610f75d47138a7a502046a650be
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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