Sodium triacetoxyborohydride → HCID 178459389, Verbindung

HRID 1412476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1412476
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.[OH:7][C:8]([CH3:19])([CH3:18])[CH2:9][O:10][CH:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:19][C:8]([OH:7])([CH3:18])[CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH:14]([NH:1][C:2]2[N:6]=[CH:5][NH:4][N:3]=2)[CH2:13][CH2:12]1

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 670089144-(2-Hydroxy-2-methylpropoxy)cyclohexanoneHCID 178418311HCID 178418311, Verbindung

Produkt 1

HCID 178459389HCID 178459389, VerbindungAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-1H-1,2,4-triazole (1.46 g) and 4-(2-hydroxy-2-methylpropoxy)cyclohexanone (3.25 g) in acetic acid (30 mL) was added sodium triacetoxyborohydride (5.53 g), and the mixture was stirred at room temperature for 15 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate-isopropyl alcohol (3:1). The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: methanol/ethyl acetate=0/100→6/94 (volume ratio)] to give colorless amorphous 2-methyl-1-{[4-(1H-1,2,4-triazol-3-ylamino)cyclohexyl]oxy}propan-2-ol (2.84 g, 64%) as a diastereomixture.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate-isopropyl alcohol (3:1)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography [eluent: methanol/ethyl acetate=0/100→6/94 (volume ratio)]

Quellen und Nachweise

ORD-Eintrag
ord-ab4077767b7e4a4fa8b71f1bde86614c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921379B2

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