Water → HCID 86702144, compound

HRID 1776213Notes

Reaction equation

HRID 1776213 reaction equation
[CH3:1][C:2]([N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)([CH:4]=[CH2:5])[CH3:3].C[N+]1([O-])CC[O:23]CC1.[OH2:27]>C(#N)C.[Os](=O)(=O)(=O)=O>[CH:17]1[C:18]2[N:6]([C:2]([CH3:1])([CH3:3])[CH:4]([OH:23])[CH2:5][OH:27])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 86702143HCID 86702143, compound

Product 1

HCID 86702144HCID 86702144, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 9-(2-methylbut-3-en-2-yl)-9H-carbazole (0.400 g, 1.7 mmol), and 4-methylmorpholine N-oxide (0.398 g, 3.4 mmol) in acetonitrile (10 mL) and water (3 mL) was added 4% osmium tetroxide solution (0.540 mL, 0.1 mmol). The mixture was stirred at room temperature for 48 hrs. The reaction was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated to give a yellow solid (0.43 g, 94%). 1H NMR (300 MHz, CDCl3) δ 8.10 (d, 2H, J=7.5 Hz), 7.84 (d, 2H, J=8.4 Hz), 7.37 (t, 2H, J=7.5 Hz), 7.23 (t, 2H, J=7.5 Hz), 4.84 (m, 1H), 3.80-3.50 (m, 2H), 2.30 (br s, 1H), 2.11 (s, 3H), 2.05 (s, 3H), 1.82 (br s, 1H). ESI m/z: 269.8 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50f6c3a890334eb0a1f76f133145c71e
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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