Water → 4-Hydroxy-1-(6-oxo-6-phenylhexyl)-4-tert-butoxycarbonylaminomethylpiperidine

HRID 344272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344272
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].C(=O)([O-])[O-].[K+].[K+].[OH:21][C:22]1([CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>CN(C)C=O>[OH:21][C:22]1([CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=[O:8])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:24][CH2:23]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10868112tert-butyl N-((4-hydroxypiperidin-4-yl)methyl)carbamateHCID 112422601-Hexanone, 6-bromo-1-phenyl-

Produkt 1

HCID 538421054-Hydroxy-1-(6-oxo-6-phenylhexyl)-4-tert-butoxycarbonylaminomethylpiperidineAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-Bromo-1-phenyl-1-hexanone (2.9 g) and potassium carbonate (3 g) were added to a solution of 4-hydroxy-4-tert-butoxycarbonylaminomethylpiperidine (2.5 g) in dimethylformamide (40 ml), and the mixture was stirred at 60° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 3.74 g of 4-hydroxy-1-(6-oxo-6-phenylhexyl)-4-tert-butoxycarbonylaminomethylpiperidine.

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-c645464eb0d84c45beb1613e171592f6
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864039

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