Water → cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine

HRID 344291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344291
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14]OS(C)(=O)=O)[C@H:10]([OH:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].O>CN(C)C=O>[N:21]([CH2:14][C@H:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C@H:10]1[OH:20])=[N+:22]=[N-:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86753635cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

Produkt 1

HCID 86657830cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidineAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of cis-1-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine (4.44 g) in dimethylformamide (60 ml) were added sodium azide (1.4 g) and ammonium chloride (1.15 g), and the resulting mixture was stirred at 60° C. for 6 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 3.4 g of cis-4-azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine.

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 residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-97df34546f294ddb8456e8f561dab525
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864039

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