Lovastatin → HCID 14164059, compound

HRID 1634625Notes

Reaction equation

HRID 1634625 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][CH2:12][C@@H:13]([C:15]([O:17][C@@H:18]1[C@@H:23]2[C@@H:24]([CH2:29][CH2:30][C@H:31]3[O:37][C:35](=[O:36])[CH2:34][C@H:33]([OH:38])[CH2:32]3)[C@@H:25]([CH3:28])[CH:26]=[CH:27][C:22]2=[CH:21][C@H:20]([CH3:39])[CH2:19]1)=[O:16])[CH3:14].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>>[CH3:14][CH:13]([CH2:12][CH3:11])[C:15]([O:17][CH:18]1[CH:23]2[C:22]([CH:27]=[CH:26][CH:25]([CH3:28])[CH:24]2[CH2:29][CH2:30][CH:31]2[CH2:32][CH:33]([OH:38])[CH2:34][CH:35]([OH:36])[O:37]2)=[CH:21][CH:20]([CH3:39])[CH2:19]1)=[O:16]

Participants

4

Reactant 3

HCID 53232LovastatinHCID 62649Sodium sulfate decahydrateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14164059HCID 14164059, compoundYield 99%

Procedure

Diisobutylaluminum hydride (1.0 M solution in dichloromethane, 99.0 ml, 99 mmol) was added dropwise to a stirred and cooled (−35° C.) solution of lovastatin (20.0 g, 49.4 mmol) in tetahydrofuran (200 ml) in a period of 1 hours. Stirring was continued for 1 hour at −35° C. Celite (20 g) and sodium sulphate decahydrate (30 g) were added. The mixture was stirred for 20 min. Cooling bath was removed and stirring was continued for 1 hour. The mixture was filtered through a pad of Celite (8.0×1.5 cm) and the solid was washed with ethyl acetate. Evaporation of the combined filtrate gave crude hemiacetals II (19.0 g, yield 99%) as a white foam (HPLC purity>96%). This was used without further purification in the next step.

Workup

  1. stirringStirring
  2. stirringThe mixture was stirred for 20 min
  3. temperatureCooling bath
  4. customwas removed
  5. stirringstirring
  6. waitwas continued for 1 hour
  7. filtrationThe mixture was filtered through a pad of Celite (8.0×1.5 cm)
  8. washthe solid was washed with ethyl acetate
  9. customEvaporation of the combined filtrate

Sources & evidence

ORD record
ord-f1cfbd948a494427ace352dd7ea27870
Source dataset
uspto-grants-2003_01
Patent number
US06506929B1

Reaction notes

Loading…