Diisobutylaluminumhydride → 4-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde

HRID 33475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33475
C([O:3][C:4]([C:6]1[O:25][C:9]2[C:10](=[O:24])[NH:11][C:12]3[C:13]([N:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:15]=[CH:16][C:17]=3[C:8]=2[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[O:24]=[C:10]1[C:9]2[O:25][C:6]([CH:4]=[O:3])=[CH:7][C:8]=2[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[C:12]=2[NH:11]1

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 597967744-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester

Produkt 1

HCID 597967754-Oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carboxylic acid ethyl ester (iv) in DCM at 0° C. is treated with diisobutylaluminum hydride (“DIBAL-H”) and is allowed to warm to room temperature. The reaction is quenched with a saturated solution of sodium potassium tartrate and partitioned. The organic layer is dried over MgSO4, filtered and treated with manganese dioxide (“MnO2”). After stirring for 16 h at room temperature, the reaction is filtered and is concentrated to give 4-oxo-6-piperidin-1-yl-4,5-dihydro-furo[2,3-c]quinoline-2-carbaldehyde (v).

Aufarbeitung

  1. customThe reaction is quenched with a saturated solution of sodium potassium tartrate
  2. custompartitioned
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with manganese dioxide (“MnO2”)
  6. filtrationthe reaction is filtered
  7. concentrationis concentrated

Quellen und Nachweise

ORD-Eintrag
ord-da03775be1b84d0aa2cf7170c8f040c1
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429603B2

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