Sodium Hydroxide → 3-[1,1-Dimethyl-2-(tetrahydropyran-2-yloxy)-ethyl]-isoxazol-5-ylamine

HRID 469757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469757
S(O)(O)(=O)=O.[OH:6][NH2:7].[CH3:8][C:9]([CH3:23])([CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1)[C:10](=O)[CH2:11][C:12]#[N:13].[OH-].[Na+]>O>[CH3:8][C:9]([C:10]1[CH:11]=[C:12]([NH2:13])[O:6][N:7]=1)([CH3:23])[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 592532944,4-Dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile

Produkt 1

HCID 592532173-[1,1-Dimethyl-2-(tetrahydropyran-2-yloxy)-ethyl]-isoxazol-5-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Hydroxyamine sulfate (0.729 g, 4.439 mmol) is added to a stirred solution of 4,4-dimethyl-3-oxo-5-(tetrahydro-pyran-2-yloxy)-pentanenitrile (2 g, 8.878 mmol) and sodium hydroxide (0.764 g, 19.1 mmol) in water (20 mL). The reaction mixture is stirred at reflux for 18 hours. After this time, the reaction mixture is cooled to room temperature and extracted with ethyl acetate. The organic layers are combined and washed with brine, dried (Na2SO4), filtered and concentrated to yield the title compound, m/z 157 [M+H+−84]. 1H NMR (400 MHz, DMSO-d) δ ppm 1.17 (6H, d), 1.45 (4H, br), 1.58 (1H, br), 1.68 (1H, br), 3.26 (1H, d), 3.4 (1H, br), 3.59 (1H, d), 3.68 (1H, br), 4.5 (1H, br), 4.88 (1H, s), 6.43 (2H, s).

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f5127ba1008b4e52ad0041caa6d8d8a7
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629157B2

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