Water → 1-(8,9-Dihydroxynonyl)-3,7-dimethylxanthine

HRID 2259422Notes

Reaction equation

HRID 2259422 reaction equation
[CH2:1]([N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].C[N+]1([O-])CC[O:27]CC1.[OH2:31].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CC(O)(C)C.CC(C)=O.O=[Os](=O)(=O)=O>[OH:31][CH:8]([CH2:9][OH:27])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH3:22])[C:11]1=[O:12]

Participants

8

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 152306351-(8-Nonenyl)-3,7-dimethylxanthine

Product 1

HCID 98408081-(8,9-Dihydroxynonyl)-3,7-dimethylxanthineYield 54%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 1-(8-nonenyl)-3,7-dimethylxanthine (CT1550 810 mg, 2.9 mmol), 4-methylmorpholine-N-oxide (340 mg, 2.9 mmol) and OsO4 (3 drops of a 2.5% solution by weight in tBuOH) in acetone (20 ml) and water (20 ml) was stirred for 24 hrs. A saturated solution of sodium dithionite (5 ml) was added to the reaction mixture which was then stirred for 15 min. The reaction mixture was extracted with 25% EtOH/dichloromethane (4×50 ml). The organic layers were combined, dried with sodium sulfate and evaporated to a white solid which was recrystalized in ethanol/chloroform to give 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (CT 1561 ) (490 mg, 54% yield).

Workup

  1. extractionThe reaction mixture was extracted with 25% EtOH/dichloromethane (4×50 ml)
  2. dry with materialdried with sodium sulfate
  3. customevaporated to a white solid which
  4. customwas recrystalized in ethanol/chloroform

Sources & evidence

ORD record
ord-69d8c78956eb483db0ab881ede9f0949
Source dataset
uspto-grants-1995_12
Patent number
US05473070

Reaction notes

Loading…