1-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide → Tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylate

HRID 742885

Reaktionsgleichung

Reaktionsgleichung von HRID 742885
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][NH:11][CH:12]([C:24]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

4

Edukt 1

HCID 190319381-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide

Produkt 1

HCID 4063013Tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylateAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1.1 g of 1-(benzyloxycarbonyl)-4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide were dissolved in 40 ml of ethanol. 0.1 g of 10% palladium-on-carbon was added and the mixture was hydrogenated at room temperature and under atmospheric pressure for 2 hours. The catalyst was filtered off. The filtrate was evaporated to give 0.74 g of crude product which was purified by flash chromatography on silica gel using 5% methanol in dichloromethane for the elution. After evaporation of the solvents there was obtained 0.44 g of 4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide as an oil; MS: m/e 286 [M+H]+.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customThe filtrate was evaporated
  3. customto give 0.74 g of crude product which
  4. customwas purified by flash chromatography on silica gel using 5% methanol in dichloromethane for the elution
  5. customAfter evaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-1acc51b13af54d929642043fa12442fa
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554756

Verknüpfte Notizen

Wird geladen…