Sodium Hydroxide → 1-[3-(Hydroxymethyl)-1-piperidinyl]-3-methyl-1-butanone

HRID 2280181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280181
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.[OH-].[Na+].[CH3:11][CH:12]([CH3:17])[CH2:13][C:14](Cl)=[O:15]>O.C1COCC1.CCOCC>[OH:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][N:1]([C:14](=[O:15])[CH2:13][CH:12]([CH3:17])[CH3:11])[CH2:2]1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 66054Isovaleryl chlorideHCID 107308Piperidin-3-ylmethanol

Produkt 1

HCID 434223971-[3-(Hydroxymethyl)-1-piperidinyl]-3-methyl-1-butanoneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of piperidin-3-ylmethanol (10 g, 86.83 mmol) in water (25 mL), was added a solution of NaOH (13.89 g, 347.31 mmol) in water (25 mL) dropwise at 0° C. The mixture was stirred for 15 minutes, after which time, a solution of 3-methylbutanoyl chloride (20.94 g, 173.66 mmol) in THF (25 mL) was added dropwise with vigorous stirring. The reaction was slowly warmed to room temperature and, upon completion was diluted with Et2O (500 mL) was added with vigouous stirring. After 15 minutes, the phases were separated, and the aqueous phase was extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over Na2SO4, concentrated under reduced pressure and flash chromatographed on silica gel (0-100% EtOAc in hexanes) to give the title compound as a colorless oil (16.27 g, 94%). MS 200 (MH+).

Aufarbeitung

  1. additionwas added with vigouous stirring
  2. waitAfter 15 minutes
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with Et2O (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure and flash
  8. customchromatographed on silica gel (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-44cf17c453484116a8c9a95e9302e2ec
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09138013B2

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