Sodium Azide → tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamate

HRID 1423412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423412
CS(O[C@@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([C@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7]1)=[N+:20]=[N-:21]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

Produkt 1

HCID 86608905tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Crude product from example C4 is dissolved in dry DMF (180 mL). After addition of sodium azide (11.7 g; 180.0 mmol) the reaction mixture is stirred for three days at 60° C. After filtration the reaction mixture is concentrated under reduced pressure, diluted with dichloromethane, extracted with water, half saturated brine and dried over MgSO4. After column chromatography on silica gel (cyclohexane/AcOEt—9:1) 11.8 g of the title compound is obtained as pale yellow oil.

Aufarbeitung

  1. filtrationAfter filtration the reaction mixture
  2. concentrationis concentrated under reduced pressure
  3. additiondiluted with dichloromethane
  4. extractionextracted with water, half saturated brine
  5. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-a8bc33571efb4c0baa92323d50b35ca6
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927557B2

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