1-Benzyl-3-methyl-4-piperidone → 1-Benzyl-3-methylpiperidin-4-ol

HRID 1821979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821979
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH:16]([CH3:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]([CH3:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 136114921-Benzyl-3-methylpiperidin-4-olAusbeute 101,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Suspend lithium aluminum hydride (0.76 g, 20.0 mmol) in dry tetrahydrofuran (10 mL) and cool to 0° C. Add, dropwise with stirring, 1-benzyl-3-methyl-piperidin-4-one (4.06 g, 20.0 mmol) in tetrahydrofuran (20 mL). After 1 hr., quench with saturated potassium sodium tartrate solution. After 20 min., extract with ethyl acetate (2×100 mL), wash the combined organic layers with aqueous NaCl solution (100 mL), dry over sodium sulfate, filter, and concentrate to obtain the title compound (4.15 g, >100%). Mass spectrum (electrospray): m/z=206.1 (M+1).

Aufarbeitung

  1. additionAdd
  2. custom, quench with saturated potassium sodium tartrate solution
  3. waitAfter 20 min.
  4. extractionextract with ethyl acetate (2×100 mL)
  5. washwash the combined organic layers with aqueous NaCl solution (100 mL)
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-86a50c836eb141109100a601ce36ef20
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608629B2

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