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 47326

Reaktionsgleichung

Reaktionsgleichung von HRID 47326
[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 It
  3. customwas purified by adsorptive silica gel
  4. additioncharged in a non-adsorptive silica gel column with hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-da61023537e6496ab9c1190c0d24d14d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699870B2

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