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

HRID 1711222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711222
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-82f02b1b6217423d817ef409d1ea8ae7
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790724B2

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