1,4-Dioxane → HCID 18767721, compound

HRID 2105656Notes

Reaction equation

HRID 2105656 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]34[CH2:21][CH2:20][C:17]([CH:22]=C)([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[N:8][C:7]=2[N:6]([CH2:24][CH2:25][CH3:26])[C:5]1=[O:27])[CH2:2][CH3:3].[O:28]1CCOCC1>CC(O)(C)C.O.O=[Os](=O)(=O)=O>[O:27]=[C:5]1[N:6]([CH2:24][CH2:25][CH3:26])[C:7]2[N:8]=[C:9]([C:14]34[CH2:21][CH2:20][C:17]([CH:22]=[O:28])([CH2:18][CH2:19]3)[O:16][CH2:15]4)[NH:10][C:11]=2[C:12](=[O:13])[N:4]1[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 18767703HCID 18767703, compound

Product 1

HCID 18767721HCID 18767721, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

1,3-Dipropyl-8-(1-vinyl-2-oxa-bicyclo[2.2.2]oct-4-yl)-3,7-dihydro-purine-2,6-dione (400 mg, 1.08 mmol) was suspended in 8 ml of dioxane and 1 ml of a 2.5% solution of OsO4 in t-BuOH was added, followed by 3 ml of H2O. After 10 min, NaIO4 was added and the reaction mixture was stirred at rt for 3 h. It was then diluted with H2O and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated to afford the aldehyde intermediate, 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-2-oxa-bicyclo[2.2.2]octane-1-carbaldehyde.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4cb3e6d4582e4a23b48fbdd0592a0874
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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