반응 #67896

반응 방정식

2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S,E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetic acid

potassium hydroxide

→

titled compound

수율 88.0%

Treprostinil

수율 88.0%

용매

methanol

반응 조건

후처리

1. 1
   기타overnight
2. 2
   기타at room temperature
3. 3
   여과Then, the reaction mixture was filtered with celite pad
4. 4
   기타The solvent was evaporated off under vacuum
5. 5
   workup.ADDITIONThe residues was diluted with 50 m ethyl acetate and 50 ml saturated sodium bicarbonate aqueous
6. 6
   기타separated
7. 7
   추출the organic layers was extracted with 50 ml saturated sodium bicarbonate aqueous
8. 8
   workup.ADDITION3N HCl was added slowly until pH=˜2
9. 9
   추출The aqueous layer was extracted with 100 ml ethyl acetate
10. 10
    건조dried over anhydrous magnesium sulfate
11. 11
    여과The solid was filtered off
12. 12
    기타The solvent was evaporated off under vacuum
13. 13
    기타The crude product was purified by crystallization

실험 절차

2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S,E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetic acid (2.5 g, 0.008 mol) in dry methanol (25 ml) was treated with potassium hydroxide (0.5 g, 0.008 mol), then with 5% Pd/C (0.5 g, 20% wt) under hydrogen overnight at room temperature. Then, the reaction mixture was filtered with celite pad. The solvent was evaporated off under vacuum. The residues was diluted with 50 m ethyl acetate and 50 ml saturated sodium bicarbonate aqueous. The mixture was phase separated and the organic layers was extracted with 50 ml saturated sodium bicarbonate aqueous. The aqueous layers were combined and then 3N HCl was added slowly until pH=˜2. The aqueous layer was extracted with 100 ml ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by crystallization. The titled compound was obtained in a crystalline form. Yield: 88%

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