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 were added N-methylmorpholine N-oxide (5.15 g), microencapsulated osmium tetraoxide (1 g, 10% osmium tetraoxide content), followed by stirring at 40-50° C. for 21 hours. Any insoluble microencapsulated osmium was filtered off, and was washed with acetonitrile. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1), to thereby give the title compound (4.97 g).

1. filtrationAny insoluble microencapsulated osmium was filtered off
2. washwas washed with acetonitrile
3. concentrationThe filtrate was concentrated under reduced pressure
4. customthe residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1)

ORD record

ord-4af616c19fea4bdabdafcb62035d3786

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576135B2