Ammonium Chloride → (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

HRID 1090506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090506
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:21]=[N+:22]=[N-:23])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3]

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

Produkt 1

HCID 57320993(2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of (2S,4R)-1-allyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (20.0 g) in N,N-dimethylformamide (200 ml) were added ammonium chloride (5.74 g) and sodium azide (6.98 g). The resulting mixture was heated at 75° C. for 8 hours. After cooling, the mixture was diluted with ethyl acetate (1 l) and aqueous sodium hydrogen carbonate (1 l). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine.

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-897b8bc684d34bdab13bb3900cec9b4d
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05081237

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