Tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylate → Tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

HRID 2300162

Reaktionsgleichung

Reaktionsgleichung von HRID 2300162
[CH2:1]([O:8][CH:9]([CH2:25][O:26]C(C)(C)C)[CH2:10][C:11]1([OH:24])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C>[CH2:1]([O:8][CH:9]([CH2:25][OH:26])[CH2:10][C:11]1([OH:24])[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 22744588Tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylateHCID 57418452Ammonium cerium-nitrate

Produkt 1

HCID 22744648Tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylateAusbeute 26,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2.36 g of tert-butyl 4-[2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylate was dissolved in 40 ml acetonitrile, 426 mg of cerium ammonium nitrate was added thereto, and the mixture was stirred at room temperature overnight. Silica gel was added to the reaction solution, and then it was evaporated. It was purified by adsorptive silica gel charged in a non-adsorptive silica gel column with hexane-ethyl acetate to give 547 mg of tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate.

Aufarbeitung

  1. additionSilica gel was added to the reaction solution
  2. customit was evaporated
  3. customIt was purified by adsorptive silica gel
  4. additioncharged in a non-adsorptive silica gel column with hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8d22fd94ad45462797cbfecb71441228
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498159B1

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