Tetrahydrofuran → HCID 69621035, compound

A solution of (+)-9-bromo-2-(t-butyldimethylsilyloxymethyl)-5,8-epoxytricyclo[5.2.1.02,6]dec-3-ene (3a′) (283 mg, 0.762 mmol) in a mixed solvent of THF (15 ml) and water (5 ml) was cooled to 0° C. and stirred. To the solution were added 4-methylmorpholine N-oxide (155 mg, 1.14 mmol) and a 0.197 M-THF solution of osmium tetraoxide (1.5 ml, 0.3 mmol). Subsequently, the mixture was allowed to warm up to room temperature and stirred overnight. A 10% aqueous solution of sodium sulfite (15 ml) was added and the mixture was filtered through Celite. The filtered product was washed thoroughly with water, THF and diethyl ether. The combined washings and filtrate were diluted with diethyl ether (80 ml). The organic layer was washed with saturated aqueous NaHCO3 and saturated aqueous NaCl, respectively, and dried over magnesium sulfate. Subsequently, the solvent was distilled off under reduced pressure to obtain the residue. Silica gel column chromatography (eluting solvent: n-hexane/diethyl ether=2/1) of the residue afforded (+)-9-bromo-2-(t-butyldimethylsilyloxymethyl)-3,4-dihydroxy-5,8-epoxytricyclo[5.2.1.02,6]decane (4a′) (246 mg, 0.607 mmol, 80% yield), with the following data:

1. stirringstirred overnight
2. filtrationthe mixture was filtered through Celite
3. washThe filtered product was washed thoroughly with water, THF and diethyl ether
4. additionThe combined washings and filtrate were diluted with diethyl ether (80 ml)
5. washThe organic layer was washed with saturated aqueous NaHCO3 and saturated aqueous NaCl
6. dry with materialrespectively, and dried over magnesium sulfate
7. distillationSubsequently, the solvent was distilled off under reduced pressure
8. customto obtain the residue
9. washSilica gel column chromatography (eluting solvent: n-hexane/diethyl ether=2/1) of the residue

ORD record

ord-81487deb540b430d9bcf958ec347ce4b

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053224B2