反应详情

温度

70 °C

The methyl ester from Example 5 (43 mg) was dissolved in 1:1 ethyl acetate/ethanol (10 mL) and filtered through a syringe filter to remove insoluble material. Platinum oxide (35 weight percent) was added and the mixture placed under 50 psi of hydrogen gas on a Parr shaker overnight. TLC analysis with 95:5 CH2Cl2/MeOH showed consumption of starting material with a more polar product having been formed. The mixture was filtered through a 0.5 μm syringe filter, washing with 1:1 EtOAc/EtOH, and the filtrate concentrated under reduced pressure to a pale red-brown glass. The crude material was redissolved in ethanol (20 mL) and 20 μL of concentrated HCl were added. The solution was warmed to 70° C. and allowed to stir overnight. TLC of the reaction mixture (96:4 CH2Cl2/MeOH) showed the formation of a new product with no remaining starting material. The reaction mixture was cooled to ambient temperature and concentrated under reduced pressure to a light orange film. This was chromatographed over silica gel eluting with 96:4 CH2Cl2/MeOH. The title product was isolated in 22% yield.

1. filtrationfiltered through a syringe
2. filtrationfilter
3. customto remove insoluble material
4. additionPlatinum oxide (35 weight percent) was added
5. customplaced under 50 psi of hydrogen gas on a Parr shaker overnight
6. customconsumption of starting material with a more polar product
7. customhaving been formed
8. filtrationThe mixture was filtered through a 0.5 μm syringe
9. filtrationfilter
10. washwashing with 1:1 EtOAc/EtOH
11. concentrationthe filtrate concentrated under reduced pressure to a pale red-brown glass
12. dissolutionThe crude material was redissolved in ethanol (20 mL)
13. addition20 μL of concentrated HCl were added
14. temperatureThe reaction mixture was cooled to ambient temperature
15. concentrationconcentrated under reduced pressure to a light orange film
16. customThis was chromatographed over silica gel eluting with 96:4 CH2Cl2/MeOH