Water → (1R,2S)-1,2-Cyclooctanediol

Temperature

45 °C

Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and 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 (4.97 g).

1. customInsoluble microcapsulated osmium tetroxide was removed by filtration
2. washwashed 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-23b67f7db84f476aba935d7a7d42e6c8

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365205B2