反应详情

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%

1. customovernight
2. customat room temperature
3. filtrationThen, the reaction mixture was filtered with celite pad
4. customThe solvent was evaporated off under vacuum
5. additionThe residues was diluted with 50 m ethyl acetate and 50 ml saturated sodium bicarbonate aqueous
6. customseparated
7. extractionthe organic layers was extracted with 50 ml saturated sodium bicarbonate aqueous
8. addition3N HCl was added slowly until pH=˜2
9. extractionThe aqueous layer was extracted with 100 ml ethyl acetate
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationThe solid was filtered off
12. customThe solvent was evaporated off under vacuum
13. customThe crude product was purified by crystallization