1-Methyl-4-piperidone → HCID 9925480, Verbindung

HRID 2084057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2084057
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Li]C(C)(C)C.[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>>[OH:26][C:23]1([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=2)[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]1

Komponenten

4

Edukt 3

HCID 740491-Methyl-4-piperidoneHCID 22732008HCID 22732008, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 9925480HCID 9925480, VerbindungAusbeute 44,1 %

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

1.5 ml of a solution of 6-bromo-1-isoproylindole (240 mg, 1 mmol) was cooled to −78 ° C., 1.7M tBuLi (1.47 ml, 2.5 mmol) was added and the mixture stirred for 7 mins. N-Methyl-4-piperidone (340.8 mg, 3 mmol) was then added and the mixture stirred for a further 10 mins. The reaction mixture was then warmed up to −20° C. and quenched with water and dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4, concentrated in vacuo and the residue purified by column chromatography on silica gel, eluting with 2% 2M ammonia/methanol in dichloromethane to give the title product (120 mg, 44%).

Aufarbeitung

  1. stirringthe mixture stirred for a further 10 mins
  2. customquenched with water and dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with 2% 2M ammonia/methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7e3fc101e50e47b884c91a5c87bbcfb7
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716837B1

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