Morpholine → (1R,2R,3aS,8bS)-2,3,3a,8b-tetrahydro-2-hydroxy-1-[(3S,1E)-3-hydroxy-4-methyl-1-octene-6-ynyl]-5-(4-morpholinobutyl)-1H-cyclopenta[b]benzofuran

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Reaction Conditions

Reaction Steps

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).

Provenance & Evidence