Ammonium formate → 1-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one

HRID 251006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251006
C([O:8][N:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])[C:10]1=[O:22])C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:21][O:20][CH:17]([O:18][CH3:19])[CH2:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:9]([OH:8])[C:10]1=[O:22]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 672725081-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-one

Produkt 1

HCID 672723451-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-oneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-one (1.61 g, 5.22 mmol) in EtOH (50 mL) was added ammonium formate (3.34 g, 52.9 mmol) and 10 wt % Pd/C (50% wet with water, 800 mg) and the mixture was stirred at room temperature for 2 hours. The mixture was vacuum filtered through celite and the cake was washed with EtOH. The solvent was removed from the filtrate under reduced pressure and the thus obtained solid was partitioned between water (10 mL) and CH2Cl2 (50 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (100% EtOAc) provided 0.75 g (66%) of 1-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one as a colorless oil. ES-MS m/z 241 (M+Na).

Aufarbeitung

  1. filtrationfiltered through celite
  2. washthe cake was washed with EtOH
  3. customThe solvent was removed from the filtrate under reduced pressure
  4. customthe thus obtained solid was partitioned between water (10 mL) and CH2Cl2 (50 mL)
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification of the crude material by column chromatography on silica gel (100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-61809e737566463f829330d5f8a38c37
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863293B2

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