Sodium Dithionite → HCID 57723935, compound

To a solution of optically pure (4aR,8aR)-2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (50 mg, 0.29 mmol) in 4.5 mL of THF-tert-BuOH—H2O (1:3:0.5) was added NMO (45 mg, 0.32 mmol) and the solution was stirred for 5 min. at ambient temperature. OsO4 (15 μL, 25 wt % in tert-BuOH) was added and the solution was stirred at ambient temperature for 4 days. Sodiumhydrosulphite (0.2 g), Florisil (2.0 g) and H2O (5 ml) were added and the mixture was stirred for 30 min, wash with acetone (100 mL), filtered through filter paper and extracted with EtOAc (80 mL×2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography with 100% EtOAc.

1. stirringthe solution was stirred at ambient temperature for 4 days
2. stirringthe mixture was stirred for 30 min
3. washwash with acetone (100 mL)
4. filtrationfiltered
5. filtrationthrough filter paper
6. extractionextracted with EtOAc (80 mL×2)
7. washThe combined organic layers were washed with brine (50 mL)
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo
10. customThe residue was purified by flash chromatography with 100% EtOAc

ORD record

ord-9ec856772065418a88a60bc772b6de9f

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550607B2