Trifluoroacetic acid → racemic (2'R,3R,4'S)-1'-[3-(4-acetyl-piperazin-1-yl)-propyl]-6-chloro-4'-(3-chlorophenyl)-2'-isopropenyl spiro[3H-indole-3,3' piperidine]-2,6'(1H)-dione
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:31])[C@:10]3([C@H: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][CH2:25][CH2:26]Cl)[C@@H:11]3[C:28]([CH3:30])=[CH2:29])[C:5]2=[CH:4][CH:3]=1.[CH3:32]OC([Si](C)(C)C)C.[N:40]1([C:46](=[O:48])[CH3:47])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.FC(F)(F)C(O)=O>>[CH3:25][CH2:24][N:12]([CH:11]([CH3:10])[CH3:28])[CH:13]([CH3:14])[CH3:32].[C:46]([N:40]1[CH2:45][CH2:44][N:43]([CH2:26][CH2:25][CH2:24][N:12]2[C:13](=[O:23])[CH2:14][CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[C:10]3([C:5]4[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[NH:8][C:9]3=[O:31])[CH:11]2[C:28]([CH3:30])=[CH2:29])[CH2:42][CH2:41]1)(=[O:48])[CH3:47]Participants
5
Reactant 3
Product 2
Procedure
In a manner similar to the method described in example 60b, (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-1′-(3-chloro-propyl)-2′-isopropenyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane prepared in example 123a (0.2 g, 0.20 mmol) was reacted with 1-piperazin-1-yl-ethanone (0.51 g, 4 mmol), trifluoroacetic acid (2 mL) and then N,N′-diisopropylethylamine (2 mL) to give racemic (2′R,3R,4′S)-1′-[3-(4-acetyl-piperazin-1-yl)-propyl]-6-chloro-4′-(3-chlorophenyl)-2′-isopropenylspiro[3H-indole-3,3′ piperidine]-2,6′(1H)-dione as a yellow solid (Yield: 95 mg, 50.8%).
Sources & evidence
- ORD record
- ord-8691cd2fbb744dbebf074dd8d0cf1592
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07495007B2
Reaction notes
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