반응 #468896

반응 방정식

simvastatin phenylboronate

→

simvastatin

수율 90.1%

용매

1,3-propanediol

반응 조건

후처리

1. 1
   workup.DISTILLATION182 mL of distillate was collected
2. 2
   온도the reaction was cooled to 20 to 25° C
3. 3
   workup.ADDITIONDeionized water (270 mL) was added
4. 4
   추출to extract the mixture
5. 5
   세척The combined toluene layers were washed with water (2×30 mL)
6. 6
   온도The organic solution was heated
7. 7
   온도at reflux for 1 hour
8. 8
   기타water was azeotropically removed
9. 9
   농축The solution was concentrated to a final volume of 24 mL under vacuum at 48 to 50° C
10. 10
    workup.ADDITIONTo the concentrated solution was added hexanes (215 mL) over 10 minutes
11. 11
    온도The resulting slurry was cooled to 0 to 5° C.
12. 12
    여과filtered
13. 13
    세척The crude simvastatin was washed with 0 to 5° C. hexanes
14. 14
    기타dried under vacuum

실험 절차

A suspension of simvastatin phenylboronate (30.0 g) and 1,3-propanediol (450 mL) was heated at 105 to 107° C. at 0.2 mm Hg. After 1 hour, 182 mL of distillate was collected and the reaction was cooled to 20 to 25° C. Deionized water (270 mL) was added and toluene (3×75 mL) was used to extract the mixture. The combined toluene layers were washed with water (2×30 mL). The organic solution was heated at reflux for 1 hour and water was azeotropically removed. The solution was concentrated to a final volume of 24 mL under vacuum at 48 to 50° C. To the concentrated solution was added hexanes (215 mL) over 10 minutes. The resulting slurry was cooled to 0 to 5° C. and filtered. The crude simvastatin was washed with 0 to 5° C. hexanes and dried under vacuum to yield 21.0 g (88%) of simvastatin.

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