Hydrazine hydrate (1:1) → tert-Butyl (4-aminobutoxy)carbamate

HRID 2066377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066377
O.NN.[C:4]([O:8][C:9]([NH:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1C(=O)C2C(=CC=CC=2)C1=O)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)C>[C:4]([O:8][C:9](=[O:10])[NH:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])([CH3:7])([CH3:5])[CH3:6]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 58690204HCID 58690204, Verbindung

Produkt 1

HCID 23136565tert-Butyl (4-aminobutoxy)carbamateAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Hydrazine hydrate (1.0 ml, 20 mmol) was added to a solution of 2-(4-(tert-butoxycarbonylaminoxy)butyl)isoindole-1,3-dione (2.08 g, 6.22 mmol) in ethanol (8.0 ml). The reaction mixture was stirred at 80° C. for 65 h. The solvent was removed in vacuo. The residue was dissolved in toluene (10 ml) and the solvent was removed in vacuo. The residue was suspended in 1 N hydrochloric acid (10 ml). The precipitation was removed by filtration and was washed with water (2 ml). The filtrate and the wash-liquids were combined and made basic with potassium carbonate. The solution was extracted with dichloromethane (4×20 ml). The organic layer was dried over magnesium sulphate. The solvent was removed in vacuo to give 0.39 g of N-(4-aminobutoxy)carbamic acid tert-butyl ester. Potassium carbonate (3 g) was added to the aqueous phase, which was extracted with dichloromethane (3×20 ml). These combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo to give another 0.39 g of N-(4-aminobutoxy)carbamic acid tert-butyl ester.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in toluene (10 ml)
  3. customthe solvent was removed in vacuo
  4. customThe precipitation
  5. customwas removed by filtration
  6. washwas washed with water (2 ml)
  7. extractionThe solution was extracted with dichloromethane (4×20 ml)
  8. dry with materialThe organic layer was dried over magnesium sulphate
  9. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-46c66449ca034e40b3f7ea982fd9428b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293708B2

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