Neopentyl glycol → Simvastatin

HRID 381715

Reaktionsgleichung

Reaktionsgleichung von HRID 381715
[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@H:22]3[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[CH2:23]3)[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:30])[CH2:10]1)=[O:7])([CH3:5])[CH3:4].C1(B([O-])[O-])C=CC=CC=1.OCC(C)(CO)C>C1(C)C=CC=CC=1>[CH3:1][CH2:2][C:3]([C:6]([O:8][C@@H:9]1[C@@H:14]2[C@@H:15]([CH2:20][CH2:21][C@H:22]3[O:28][C:26](=[O:27])[CH2:25][C@H:24]([OH:29])[CH2:23]3)[C@@H:16]([CH3:19])[CH:17]=[CH:18][C:13]2=[CH:12][C@H:11]([CH3:30])[CH2:10]1)=[O:7])([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 31344Neopentyl glycolHCID 86757524Simvastatin phenylboronate

Produkt 1

HCID 54454SimvastatinAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

A mixture of simvastatin phenylboronate (5.22 g, 0.010 mol), toluene (31 mL), and neopentyl glycol (1.11 g, 0.0107 mol) was heated under a nitrogen atmosphere at 77 to 79° C. for 1 hour and 40 minutes. The solution was concentrated under reduced pressure at a bath temperature of 60° C. to a final volume of 5 mL and n-heptane (160 mL) was added at a temperature of 50-60° C. The crude simvastatin was filtered and washed with heptane to provide 3.17 g (76%) of simvastatin. By appropriate manipulation of the conditions and reagents, compounds such as the compactin analogue of simvastatin may be prepared.

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure at a bath temperature of 60° C. to a final volume of 5 mL and n-heptane (160 mL)
  2. additionwas added at a temperature of 50-60° C
  3. filtrationThe crude simvastatin was filtered
  4. washwashed with heptane

Quellen und Nachweise

ORD-Eintrag
ord-afe2da7b478542919f4f3df49a527291
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307066B1

Verknüpfte Notizen

Wird geladen…