Reaktion #462655

Reaktionsgleichung

sodium hydroxide

(4RS,4aSR,7aRS)-4-hydroxy4-phenyl-6-benzylperhydrothiopyrano[2,3-c]pyrrole

→

(4aRS,7aRS)-6-benzyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole

Ausbeute 85.8%

Lösungsmittel

benzene

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is refluxed for 1 hour
2. 2
   Sonstigebrought to 20° C.
3. 3
   Temperaturcooled solution
4. 4
   SonstigeThe suspension obtained
5. 5
   Filtrationis filtered
6. 6
   Sonstigethe filtrate is decanted
7. 7
   Waschenthe organic phase is washed with 200 cm3 of a saturated aqueous solution of sodium chloride
8. 8
   Trocknendried over magnesium sulphate
9. 9
   Einengenconcentrated to dryness under reduced pressure (2.7 kPa)
10. 10
    SonstigeThe oil obtained
11. 11
    Sonstigeis chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 5.2 cm, height 39 cm)
12. 12
    Wascheneluting under a nitrogen pressure of 0.6 bar
13. 13
    Sonstigewith a cyclohexane and ethyl acetate mixture (90/10 by volume) and collecting fractions of 125 cm 3
14. 14
    Einengenconcentrated to dryness under reduced pressure (2.7 kPa)
15. 15
    SonstigeThe oil obtained
16. 16
    Sonstigeis crystallized from 200 cm3 of diisopropyl oxide
17. 17
    Sonstigedried

Vorschrift

43.7 g of zirconium tetrachloride are added to a solution of 12.2 g of (4RS,4aSR,7aRS)-4-hydroxy4-phenyl-6-benzylperhydrothiopyrano[2,3-c]pyrrole in 180 cm3 of benzene. The reaction mixture is refluxed for 1 hour and then brought to 20° C. and diluted with 200 cm3 of dichloromethane. 150 cm3 of a 4N aqueous solution of sodium hydroxide are added to the resulting cooled solution. The suspension obtained is filtered, the filtrate is decanted, the organic phase is washed with 200 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 5.2 cm, height 39 cm), eluting under a nitrogen pressure of 0.6 bar, with a cyclohexane and ethyl acetate mixture (90/10 by volume) and collecting fractions of 125 cm 3. Fractions 19 to 32 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is crystallized from 200 cm3 of diisopropyl oxide, the crystals are drained and dried. 6.2 g of (4aRS,7aRS)-6-benzyl-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole are obtained in the form of orange-colored crystals; melting point 130° C.

Quelle