Water → HCID 21949857, compound

HRID 558291Notes

Reaction equation

HRID 558291 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([N:10]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[C:21]([CH:24]=2)[C:22]#[N:23])[C:12]([C:27]([CH3:30])([CH3:29])[CH3:28])=[N:11]1)[CH:8]=C.[OH2:31].[BH4-].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[C:27]([C:12]1[C:13]([O:16][C:17]2[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[C:21]([CH:24]=2)[C:22]#[N:23])=[C:14]([CH3:15])[N:10]([CH2:7][CH2:8][OH:31])[N:11]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21949849HCID 21949849, compoundHCID 23667635Sodium periodate

Product 1

HCID 21949857HCID 21949857, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

Sodium periodate (1.00 g, 4.60 mmol), osmium tetroxide (1.5% solution in tert-butanol, 190 mg, 0.02 mmol) and the pyrazole from Example 156 (600 mg, 1.86 mmol) were dissolved in acetone (9 ml) and water (3 ml) under nitrogen at room temperature, and the reaction was stirred for 5 hours. The acetone was removed under reduced pressure and the residue was extracted with ethyl acetate (30 ml). The organic phase was washed with water (2×30 ml) then brine (30 ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude aldehyde was then dissolved in methanol (15 ml) and sodium borohydride (84 mg, 2.22 mmol) was added portionwise at room temperature under nitrogen. The reaction was stirred for 3 hours and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (10 ml) and water (10 ml) and the organic phase was washed with water (2×10 ml) then brine (10 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was purified by flash chromatography on silica gel eluting with a solvent gradient of pentane changing to ethyl acetate:pentane (50:50, by volume) to provide the title compound (250 mg) as a colourless oil.

Workup

  1. customThe acetone was removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate (30 ml)
  3. washThe organic phase was washed with water (2×30 ml)
  4. dry with materialbrine (30 ml), dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude aldehyde was then dissolved in methanol (15 ml)
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was partitioned between ethyl acetate (10 ml) and water (10 ml)
  9. washthe organic phase was washed with water (2×10 ml)
  10. dry with materialbrine (10 ml), dried over magnesium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customThe residual oil was purified by flash chromatography on silica gel eluting with a solvent gradient of pentane changing to ethyl acetate:pentane (50:50, by volume)

Sources & evidence

ORD record
ord-8c150dd9483546fe9c44996d984776d8
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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