1,4-Dioxane → 9-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-one

To a 1,4-dioxane solution containing N-ethylpiperidine hypophosphite (1.25 mL, 2.2 mmol) at a concentration of 1.764 mol/L, a mixed solution of a tetrahydrofuran solution (2 mL) of 2′,3′-bis-O-[(methylthio)thiocarbonyl]inosine (99 mg, 0.22 mmol) and a triethylborane hexane solution (0.22 mL, 0.22 mmol) at a concentration of 1.0 mol/L was added, and the obtained mixture was stirred at room temperature for one hour. The obtained reaction mixture was diluted with ethyl acetate. The resultant organic layer was washed with brine solution, and thereafter dried over anhydrous magnesium sulfate and concentrated under reduced pressure. After purification by chromatography (using as eluting solutions a mixed solvent of hexane and ethyl acetate (3:7), ethyl acetate, and a mixed solvent of dichloromethane and methanol (10:1) successively in this order), 47 mg of the intended product was obtained in a yield of 92%.

1. customThe obtained reaction mixture
2. washThe resultant organic layer was washed with brine solution
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customAfter purification by chromatography (
6. washas eluting solutions a mixed solvent of hexane and ethyl acetate (3:7), ethyl acetate

ORD record

ord-cdd400be304e40c9aafa970905d2eb90

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252920B2