Aluminium lithium hydride → 1,4-Dioxa-10-azadispiro[4.2.4.2]tetradecane

HRID 1056622

Reaktionsgleichung

Reaktionsgleichung von HRID 1056622
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:11]2([CH2:21][CH2:20][C:14]3([CH2:18][CH2:17][NH:16][C:15]3=O)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1>C1COCC1>[O:7]1[C:11]2([CH2:21][CH2:20][C:14]3([CH2:18][CH2:17][NH:16][CH2:15]3)[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

Produkt 1

HCID 826579751,4-Dioxa-10-azadispiro[4.2.4.2]tetradecaneAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of LiAlH4 (21 g, 558.56 mmol) in anhydrous THF (500 mL) was added a solution of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (59 g, 279.28 mmol) in anhydrous THF (400 mL) dropwise at 0° C. in 1 h. The reaction mixture was heated to reflux and stirred for 2 h, then quenched with water at 0° C. until no bubble escaped and filtered. The filtere cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL). The filterate was concentrated in vacuo and the residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10) to give the product as a yellow solid (52 g, 94%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customquenched with water at 0° C. until no bubble
  4. filtrationfiltered
  5. washThe filtere cake was washed with a mixture of DCM and MeOH (1/1 (v/v), 500 mL)
  6. concentrationThe filterate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10)

Quellen und Nachweise

ORD-Eintrag
ord-41fa70e326314731b570a50811dbc8b5
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399637B2

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