Reaktion #502086

ord-ae05c6e12d1f40a1be49aa744b0431b9

Reaktionsgleichung

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2
→
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulonic acid

Edukte

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2

Reagenzien

Keine

Lösungsmittel

O
water
—
NaH2PO4.H2O
CC#N.O
CH3CN—H2O

Reaktionsbedingungen

Temperatur
2.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe mixture warmed to room temperature
  2. 2
    SonstigeThe reaction is quenched by addition of Na2S2O5 (380 mg)
  3. 3
    Extraktionextracted with ethyl acetate
  4. 4
    ExtraktionThe organic extract
  5. 5
    Waschenis washed with water and brine
  6. 6
    Trocknendried (Na2SO4)
  7. 7
    Filtrationfiltered
  8. 8
    Einengenconcentrated

Vorschrift

The betulone aldehyde prepared from the last step is dissolved in a mixture of NaH2PO4.H2O (877 mg) and CH3CN—H2O (17 mL) and the suspension cooled to 0-5° C. 30% aqueous H2O2 (220 μL) and a solution of NaClO2 (200 mg) in water (16 mL) are then successively added, the mixture warmed to room temperature and stirred at this temperature for 1 h. The reaction is quenched by addition of Na2S2O5 (380 mg), and extracted with ethyl acetate. The organic extract is washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue is then subjected to column chromatography to afford betulonic acid (550 mg) as white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088757B2uspto-grants-2012_01