tert-butyl (2R)-2-(azidomethyl)pyrrolidine-1-carboxylate → Ammonia

HRID 567823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567823
[N:1]([CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N+]=[N-]>[Pd].C(O)C>[NH3:1].[NH2:1][CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Komponenten

5

Edukt 1

HCID 13008760tert-butyl (2R)-2-(azidomethyl)pyrrolidine-1-carboxylate

Produkt 2

HCID 222AmmoniaHCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

10% Palladium on charcoal (750 mg) was added to a solution of tert-butyl (2R)-2-(azidomethyl)-1-pyrrolidinecarboxylate (preperation 51)(5.74 g, 25.39 mmol) in ethanol (100 ml). The reaction mixture was hydrogenated @15 psi for 2.5 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:0.5) as the eluant, to afford the title compound and some starting material. The mixture was dissolved in ethanol (100 ml) and 10% palladium on charcoal (500 mg) was added, the mixture was hydrogenated at 30 psi for 18 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure to afford the title compound as a clear oil, 4.32 g, (85%).

Aufarbeitung

  1. customfor 2.5 hrs
  2. filtrationafter which time the catalyst was filtered off
  3. customthe solvent evaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ce99e8d979f744f7833d64da1ac98e6f
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180627B2

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