Water → (1R,2S)-1,2-Cyclooctanediol

HRID 1392735Notes

Reaction equation

HRID 1392735 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 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).

Workup

  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)

Sources & evidence

ORD record
ord-992deafe31bf4d49a3836e6cd2cd1d77
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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