Water → (1R,2S)-1,2-Cyclooctanediol

HRID 459479Notes

Reaction equation

HRID 459479 reaction equation
[CH:1]1CC[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C[N+]1([O-])[CH2:15][CH2:14][O:13]CC1.[OH2:17]>C(#N)C.[Os](=O)(=O)(=O)=O>[C@@H:14]1([OH:13])[CH2:15][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C@@H:1]1[OH:17]

Participants

6

Reactant 3

HCID 962WaterHCID 136091-CycloocteneHCID 82029Methyl morpholine oxide

Product 1

HCID 10888034(1R,2S)-1,2-Cyclooctanediol

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

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 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 (4.97 g) as a colorless solid.

Workup

  1. customInsoluble microcapsulated osmium tetroxide was removed by filtration
  2. washwas 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)

Sources & evidence

ORD record
ord-a208a3bfb2bf47e1bdb62b32909e450c
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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