Sodium Hydroxide → HCID 67284959, Verbindung

HRID 1618792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618792
[CH3:1][C:2]1([CH3:23])[O:22][CH2:21][C:5]2([C:13]3[C:8](=[CH:9][C:10]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)=[CH:11][CH:12]=3)[NH:7][C:6]2=O)[CH2:4][O:3]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:23])[O:3][CH2:4][C:5]2([C:13]3[C:8](=[CH:9][C:10]([N:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)=[CH:11][CH:12]=3)[NH:7][CH2:6]2)[CH2:21][O:22]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 67284582HCID 67284582, Verbindung

Produkt 1

HCID 67284959HCID 67284959, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indolin]-2′-one (0.11 g, 0.35 mmol) in toluene (14 mL) was added sodium bis(2-methoxyethoxy)aluminium hydride (60% in toluene, 0.53 mL, 1.74 mmol). After stirring at 80° C. for 40 min, the solution was poured into a mixture of ice and 2N NaOH. The product was extracted with DCM and the combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. Purification by column chromatography (eluting with a gradient of 5-60% EtOAc in hexanes) gave 2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indoline] as a white solid. Mass Spectrum (ESI) m/e=305.2 (M+1).

Aufarbeitung

  1. extractionThe product was extracted with DCM
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by column chromatography (
  6. washeluting with a gradient of 5-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d26d51b5318647488b097138cc43d970
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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