반응 #462655

반응 방정식

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

수율 85.8%

용매

benzene

dichloromethane

반응 조건

후처리

1. 1
   온도The reaction mixture is refluxed for 1 hour
2. 2
   기타brought to 20° C.
3. 3
   온도cooled solution
4. 4
   기타The suspension obtained
5. 5
   여과is filtered
6. 6
   기타the filtrate is decanted
7. 7
   세척the organic phase is washed with 200 cm3 of a saturated aqueous solution of sodium chloride
8. 8
   건조dried over magnesium sulphate
9. 9
   농축concentrated to dryness under reduced pressure (2.7 kPa)
10. 10
    기타The oil obtained
11. 11
    기타is chromatographed on a silica gel column (0.04 mm-0.06 mm, diameter 5.2 cm, height 39 cm)
12. 12
    세척eluting under a nitrogen pressure of 0.6 bar
13. 13
    기타with a cyclohexane and ethyl acetate mixture (90/10 by volume) and collecting fractions of 125 cm 3
14. 14
    농축concentrated to dryness under reduced pressure (2.7 kPa)
15. 15
    기타The oil obtained
16. 16
    기타is crystallized from 200 cm3 of diisopropyl oxide
17. 17
    기타dried

실험 절차

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.

출처