Tetrahydrofuran → 2-(N-Boc-aminooxy)-2-methylpropan-1-ol

HRID 79001Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79001
C([O:3][C:4](=O)[C:5]([O:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:7])[CH3:6])C.[AlH4-].[Li+].O1CCCC1>C(OCC)C>[C:10]([NH:9][O:8][C:5]([CH3:7])([CH3:6])[CH2:4][OH:3])([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 28112Lithium aluminum hydrideHCID 108243852-(N-Boc-aminooxy)isobutyric acid ethyl ester

Produkt 1

HCID 108458992-(N-Boc-aminooxy)-2-methylpropan-1-olAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(N-Boc-aminooxy)isobutyric acid ethyl ester (2.35 g, 9.5 mmol) in anhydrous ethyl ether (100 mL) at 0° C. under nitrogen was added 1.0 M lithiumtetrahydroaluminate in tetrahydrofuran (17.1 mL, 17 mmol), and the reaction mixture stirred at 0° C. for 5 hours. The reaction mixture was quenched with water (25 mL) and allowed to warm to room temperature. The suspension was filtered and the residue washed with diethyl ether and layers separated. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid (1.94 g, 99%). 1H NMR (CDCl3, 400 MHz) 3.40 (s, 2H), 1.50 (s, 9H), 1.20 (s, 6H).

Aufarbeitung

  1. customThe reaction mixture was quenched with water (25 mL)
  2. temperatureto warm to room temperature
  3. filtrationThe suspension was filtered
  4. washthe residue washed with diethyl ether and layers
  5. customseparated
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35e1f6823c8d4c0cacedf4d796d1529d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841462B2

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