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

HRID 1727994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727994
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[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)=[O:26])[CH:11]3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[C:5]2=[CH:4][CH:3]=1.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[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:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 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)-dione

Produkt 1

HCID 73315581racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-1'-[(hydroxycarbonyl)-methyl]-2'-(2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of 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 (0.21 g, 0.4 mmol) prepared in 29b in the mixture of methanol (10 mL) and tetrahydrofuran (20 mL) was added aqueous NaOH solution (1N, 10 mL, 10 mmol). The reaction mixture was stirred at room temperature for overnight and then concentrated. The residue was neutralized to “pH” ˜7, then extracted with ethyl acetate. The organic layer was separated, washed with H2O, brine, dried over MgSO4 and concentrated to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-[(hydroxycarbonyl)-methyl]-2′-(2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white foam.

Aufarbeitung

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7bcdc78ee2964eceb69bed4f5ad49a1a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495007B2

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