Tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate → tert-Butyl 3-hydroxy-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

HRID 2300164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300164
C([O:8][CH:9]1[CH2:13][C:12]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[O:11][CH2:10]1)C1C=CC=CC=1.[H][H]>O1CCCC1.[C].[Pd]>[OH:8][CH:9]1[CH2:13][C:12]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[O:11][CH2:10]1

Komponenten

5

Edukt 2

HCID 22744533Tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22744549tert-Butyl 3-hydroxy-1-oxa-8-azaspiro[4.5]decane-8-carboxylateAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6.47 g of tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate was dissolved in 100 ml tetrahydrofuran, 1.3 g palladium carbon was added thereto, and the mixture was stirred overnight in a hydrogen atmosphere. The catalyst was filtered off from the reaction solution, 1.3 g of palladium carbon was added thereto, and the solution was stirred overnight in a hydrogen atmosphere. The catalyst was filtered off from the reaction solution, 2.6 g of palladium carbon was added thereto, and the solution was stirred overnight in a hydrogen atmosphere at 4.2 atmospheric pressure. The catalyst was filtered off from the reaction solution, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give 4.27 g of tert-butyl 3-hydroxy-1-oxa-8-azaspiro[4.5]decane-8-carboxylate.

Aufarbeitung

  1. filtrationThe catalyst was filtered off from the reaction solution, 1.3 g of palladium carbon
  2. additionwas added
  3. filtrationThe catalyst was filtered off from the reaction solution, 2.6 g of palladium carbon
  4. additionwas added
  5. stirringthe solution was stirred overnight in a hydrogen atmosphere at 4.2 atmospheric pressure
  6. filtrationThe catalyst was filtered off from the reaction solution
  7. customthe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-9568fe80ede14ae1be604142cfec6a1f
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498159B1

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