Acetone → HCID 10221386, compound

HRID 1954116Notes

Reaction equation

HRID 1954116 reaction equation
[CH2:1]([N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8])[CH2:2]CC=C.C[N+]1([O-])CC[O:23]CC1.S([O-])([O-])=O.[Na+].[Na+].[CH3:33][C:34]([CH3:36])=[O:35]>O>[OH:35][CH:34]([CH2:36][OH:23])[CH2:33][CH2:2][CH2:1][N:6]1[C:15](=[O:16])[C:14]2[N:13]([CH3:17])[CH:12]=[N:11][C:10]=2[N:9]([CH3:18])[C:7]1=[O:8]

Participants

6

Reactant 4

HCID 180AcetoneHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 13298150HCID 13298150, compound

Product 1

HCID 10221386HCID 10221386, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(4-pentenyl)-3,7-dimethylxanthine (2.48 g, 10 mmol), 4-methylmorpholine-N-oxide (1.49 g, 12.7 mmol) and potassium osmate dihydrate (7.3 mg; 0.02 mmol) in acetone (20 mL) and water (5 mL) was stirred for 6 hours. A solution of 20% aqueous sodium sulphite (10 ml) was added and stirred for 30 minutes. The reaction mixture was extracted with 25% ethanol/dichloromethane (4×250 mL). The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using ethyl acetate eluant to yield 2.5 g (88% yield) of 1-(4,5-dihydroxypentyl)-3,7-dimethylxanthine (inventive compound no. 1584).

Workup

  1. extractionThe reaction mixture was extracted with 25% ethanol/dichloromethane (4×250 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product obtained
  5. customwas further purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-66fbbb5f134447c2915ecf574bbb4fe4
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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