Ammonium Chloride → 6-chloro-4'-(3-chlorophenyl)-2'-(1-ethyl-1-hydroxy-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728049
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[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])[NH:12][CH:11]3[C:24](=[O:27])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1.[CH2:29]([Mg]Cl)[CH3:30].[NH4+].[Cl-]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:28])[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])[NH:12][CH:11]3[C:24]([CH2:29][CH3:30])([OH:27])[CH2:25][CH3:26])[C:5]2=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 76568170HCID 76568170, VerbindungHCID 178461633HCID 178461633, Verbindung

Produkt 1

HCID 765680146-chloro-4'-(3-chlorophenyl)-2'-(1-ethyl-1-hydroxy-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-propionylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (100 mg, 0.24 mmol) prepared in example 103 in tetrahydrofuran (3 mL) at −78° C. was added a tetrahydrofuran solution of ethylmagnesium chloride (2M, 6 mL, 12 mmol). The reaction mixture was stirred at −78° C. for 0.5 h, then slowly warmed to room temperature and stirred for 2 h. The mixture was poured into saturated aqueous NH4Cl solution, and the mixture was extracted with ethyl acetate. The organic layer was separated, dried over MgSO4, concentrated. The residue was purified by chromatography (EtOAc:MeOH=10:1) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-ethyl-1-hydroxy-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 100 mg, 93%)

Aufarbeitung

  1. temperatureslowly warmed to room temperature
  2. stirringstirred for 2 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (EtOAc:MeOH=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-d8e6517fa2334e66b5ff9259661aa145
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495007B2

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