Morpholine → HCID 69659315, Verbindung

Temperatur

50 °C

10 mg of (1R,2R,3aS,8bS)-2,3,3a,8b-tetrahydro-2-hydroxy-1-[(3S,1E)-3-hydroxy-4-methyl-1-octene-6-ynyl]-5-(3-carboxypropyl)-1H-cyclopenta[b]benzofuran was taken and was dissolved in 2 mL of dimethylformamide. After addition of 8.1 mg of 1,1′-carbonyldiimidazole, it was stirred at 50° C. for 1 hour. It was cooled to ambient temperature, and 50 mg morpholine was added. After stirring at 50° C. for 1 hour, an aqueous solution saturated with ammonium chloride was added and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and dried with anhydrous sodium sulfate. After filtration and concentration, 2 mL of tetrahydrofurane was added. While stirring on ice, 9.5 mg of lithium aluminium hydride was added and stirring continued at 0° C. for 15 minutes, then at 50° C. for 1 hour. While stirring at ambient temperature, 100 μL of an aqueous solution saturated with sodium sulfate was added, then 400 mg of anhydrous sodium sulfate was added, and stirred for 1 hour. A filtration was performed over celite, and after washing the residue with ethyl acetate, the filtrate was concentrated and subjected to a silicagel column chromatography, to obtain 5.3 mg of the compound presented in the title (48% yield).

1. temperatureIt was cooled to ambient temperature
2. stirringAfter stirring at 50° C. for 1 hour
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with a saturated saline solution
5. dry with materialdried with anhydrous sodium sulfate
6. filtrationAfter filtration and concentration, 2 mL of tetrahydrofurane
7. additionwas added
8. stirringWhile stirring on ice, 9.5 mg of lithium aluminium hydride
9. additionwas added
10. stirringstirring
11. waitcontinued at 0° C. for 15 minutes
12. waitat 50° C. for 1 hour
13. stirringWhile stirring at ambient temperature
14. addition100 μL of an aqueous solution saturated with sodium sulfate was added
15. addition400 mg of anhydrous sodium sulfate was added
16. stirringstirred for 1 hour
17. filtrationA filtration
18. washafter washing the residue with ethyl acetate
19. concentrationthe filtrate was concentrated

ORD-Eintrag

ord-a4f667ad199b4df4a69d9ad291606bb7

Quelldatensatz

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07071359B1