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

HRID 1727992Notes

Reaction equation

HRID 1727992 reaction equation
C(OC([N:8]1[C:41]2[C:36](=[CH:37][CH:38]=[C:39]([Cl:42])[CH:40]=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][C:25]([O:27][CH3:28])=[O:26])[CH:11]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[C:9]1=[O:43])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:42][C:39]1[CH:40]=[C:41]2[NH:8][C:9](=[O:43])[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][CH3:28])=[O:26])[CH:11]3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[C:36]2=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 909346066-Chloro-4'-(3-chlorophenyl)-2,3-dihydro-1'-[(methoxycarbonyl)-methyl]-2'-(2-methylphenyl)-2,6'-dioxo spiro[indole-3,3'-piperidine]-1-carboxylic acid tert-butyl ester

Product 1

HCID 131727320racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-[(methoxycarbonyl)-methyl]-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 68%

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)-2,3-dihydro-1′-[(methoxycarbonyl)-methyl]-2′-(2-methylphenyl)-2,6′-dioxospiro[indole-3,3′-piperidine]-1-carboxylic acid tert-butyl ester (0.37 g, 0.59 mmol) prepared in example 29a was reacted with trifluoroacetic acid (20 mL) in dichlormethane to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-[(methoxycarbonyl)-methyl]-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield: 0.21 g, 67%).

Sources & evidence

ORD record
ord-f5c419acd25043929d3d1cc39230bbcc
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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