Sodium hydride → 1-Boc-4-(2-pyridyloxy)piperidine

HRID 23951

Reaktionsgleichung

Reaktionsgleichung von HRID 23951
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 156199202-Chloropyridine--hydrogen chloride (1/1)

Produkt 1

HCID 219060391-Boc-4-(2-pyridyloxy)piperidineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-t-Butoxycarbonyl-4-piperidinol (5.0 g 24.88 mmol) in dry dimethylformamide (60 ml) was treated with sodium hydride (60% 2.99 g 74.75 mmol) at room temperature under argon and then with 2-chloropyridine hydrochloride (4.1 g 27.33 mmol). Then mixture was heated at 80° C. overnight. After cooling the reaction was carefully quenched with water (5 ml) and then diluted with more water (20 ml) and extracted with ethyl acetate (30 ml). The organic solution was washed with sat. sodium bicarbonate, dried (MgSO4) and evaporated to give 1-t-butoxycarbonyl-4-(2-pyridoxy)piperidine (4.96 g 72%).

Aufarbeitung

  1. temperatureAfter cooling the reaction
  2. customwas carefully quenched with water (5 ml)
  3. additiondiluted with more water (20 ml)
  4. extractionextracted with ethyl acetate (30 ml)
  5. washThe organic solution was washed with sat. sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-390aae966993417181c270dae2276020
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855715B1

Verknüpfte Notizen

Wird geladen…