Reaktion #501455

ord-42dfb6d64921409b843d06906f4bf799

Reaktionsgleichung

[BH4-].[Na+]
NaBH4
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
Artemisinin
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
compound 3
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
Artemisinin
CC(=O)O.CO
AcOH MeOH
[BH4-].[Na+]
NaBH4
→
C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3
white needles
Ausbeute 75.0%
C[C@H]1[C@@H](O)O[C@@H]2OC3(C)CC[C@H]4[C@H](C)CC[C@@H]1[C@@]24OO3
Dihydroartemisinin
Ausbeute 75.0%

Edukte

[BH4-].[Na+]
NaBH4
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
Artemisinin
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
compound 3
C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@@H]3O[C@]4(C)CC[C@@H]1[C@]32OO4
Artemisinin
CC(=O)O.CO
AcOH MeOH
[BH4-].[Na+]
NaBH4

Reagenzien

Keine

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeevaporated to dryness under reduced pressure
  2. 2
    ExtraktionThe white residue was extracted 3 times with 50 mL of EtOAc
  3. 3
    Filtrationfiltered
  4. 4
    Sonstigeevaporated to dryness

Vorschrift

Artemisinin (compound 3) (0.5 g, 1.8 mmole) in 40 mL of MeOH was cooled in an ice-bath to 0°-5° C. To the solution was added in small portions 0.25 g (6.6 mmole) of NaBH4 over a period of 30 minutes. The solution was stirred at 0°-5° C. for 2 hours after the addition of NaBH4 was complete. The solution was neutralized with 30% AcOH/MeOH and evaporated to dryness under reduced pressure. The white residue was extracted 3 times with 50 mL of EtOAc. The EtOAc extracts were combined, filtered, and evaporated to dryness to give 0.38 g (75%) of white needles mp 152°-154° C. (dec). Recrystallization from EtOAc-hexane raised the melting point to 153°-155° C. (lit. mp 153°-154° C.).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04791135uspto-grants-1988_12