Water → 4-[4-(t-Butoxycarbonylamino)methyl-4-hydroxypiperidin-1-yl]pyridine 1-Oxide

HRID 25039

Reaktionsgleichung

Reaktionsgleichung von HRID 25039
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([OH:16])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[CH:23]=[CH:22][N+:21]([O-:24])=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+].O>C(O)CC(C)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1([OH:16])[CH2:11][CH2:12][N:13]([C:18]2[CH:23]=[CH:22][N+:21]([O-:24])=[CH:20][CH:19]=2)[CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 707244-chloropyridine N-oxideHCID 516892Sodium BicarbonateHCID 10868112tert-butyl N-((4-hydroxypiperidin-4-yl)methyl)carbamate

Produkt 1

HCID 110346584-[4-(t-Butoxycarbonylamino)methyl-4-hydroxypiperidin-1-yl]pyridine 1-OxideAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31260Isoamyl AlcoholLösungsmittel

Versuchsvorschrift

To a suspension in isoamyl alcohol (35 ml) of conventionally known compounds: 4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine (2.00 g) and 4-chloropyridine 1-oxide (1.12 g), was added sodium hydrogencarbonate (1.75 g) and the mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool and water was added thereto. The reaction mixture was extracted with methylene chloride and the organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1) to obtain the title compound (1.03 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. extractionThe reaction mixture was extracted with methylene chloride
  5. washthe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

Quellen und Nachweise

ORD-Eintrag
ord-784990b1458d4facbd2c0e6fab5babbd
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858599B2

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