Water → cis-1,2-Cycloheptanediol

Temperature

45 °C

Cycloheptene (3.85 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g), microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) was added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and the insoluble substance was washed with acetonitrile and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.77 g) as a colorless solid.

1. customInsoluble microcapsulated osmium tetroxide was removed by filtration
2. washthe insoluble substance was washed with acetonitrile
3. concentrationthe filtrate was concentrated under reduced pressure
4. customThe residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

ORD record

ord-41bcfb5306e748c4b762f62d5f559c8b

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935824B2