Sodium periodate → HCID 83878940, compound

HRID 1054986Notes

Reaction equation

HRID 1054986 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=C(C)C)=[N:5][C:4]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:3]1.I([O-])(=O)(=O)=[O:18].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH3:1][N:2]1[C:6]([CH:7]=[O:18])=[N:5][C:4]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:3]1

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 90026055HCID 90026055, compound

Product 1

HCID 83878940HCID 83878940, compoundYield 99.9%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(1-methyl-5-(2-methylprop-1-enyl)-1H-1,2,4-triazol-3-yl)piperidine (376 mg, 1.71 mmol, Eq: 1.00), sodium periodate (1.46 g, 6.83 mmol, Eq: 4), osmium tetroxide 4% aq. (325 mg, 325 μl, 51.2 μmol, Eq: 0.03) and benzyltriethylammonium chloride (155 mg, 683 μmol, Eq: 0.4) in dioxane (17.9 ml) and water (4.12 ml) was stirred for 1.5 hours at 70° C. The mixture was diluted with ethyl acetate and washed 2× with water and brine. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording 2-methyl-5-piperidin-1-yl-2H-[1,2,4]triazole-3-carbaldehyde (331 mg, 99.9%) as a brown waxy solid. MS: m/z=195.4 (M+H+)

Workup

  1. washwashed 2× with water and brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-7c9892e12ca14bd382fce9728a875544
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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