Water → 1-(6-Ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazine

HRID 1831474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831474
CC(C[AlH]CC(C)C)C.[CH2:10]([O:12][C:13]1[N:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH3:34])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[CH:20][C:14]=1[C:15](OCC)=[O:16])[CH3:11].O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:10]([O:12][C:13]1[N:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:28][CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH2:32]2)(=[O:26])=[O:25])=[CH:20][C:14]=1[CH:15]=[O:16])[CH3:11]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

Produkt 1

HCID 220522361-(6-Ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazineAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

DIBAL-H (14.8 mL) was added dropwise to a solution of ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinate (5.0 g, 13.5 mmol; prepared as described in WO 99/54333) in toluene (100 mL) at −78° C. under nitrogen. The mixture was held at −78° C. for 1 hour and then water (20 mL) was added dropwise. The mixture was allowed to warm to room temperature and then water (200 mL) and ethyl acetate (200 mL) were added. The organic layer was separated and the aqueous phase re-extracted. The combined organics were washed with brine and concentrated under vacuum to give the product as a brown oil (1.64 g, 36%).

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous phase re-extracted
  3. washThe combined organics were washed with brine
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e7096e0e4b764a05b9294c9055db19de
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067660B2

Notizen zur Reaktion

Wird geladen…