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

HRID 361491

Reaktionsgleichung

Reaktionsgleichung von HRID 361491
[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+]>C(O)(C)(C)C.CC(C)=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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6386tert-ButanolKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 1-(8-nonenyl)-3,7-dimethylxanthine (810 mg, 2.7 mmol), 4-methylmorpholine-N- oxide (340 mg, 2.9 mmol) and 2.5% oxmium tetroxide in t-butanol (3 drops) in acetone (20 mL) and water (20 mL) was stirred for 24 hours. Saturated aqueous sodium dithionite solution (5 mL) was added. After stirring for 15 minutes, the reaction was extracted with 25% ethanol-dichloromethane (4×50 mL). The combined organic portions were dried over sodium sulfate, and the solvents were evaporated under vacuum. The solid residue was recrystallized (ethanol-chloroform), yielding 490 mg (54%) 1-(8,9-dihydroxynonyl)-3,7-dimethylxanthine (inventive compound no. 1561).

Aufarbeitung

  1. extractionthe reaction was extracted with 25% ethanol-dichloromethane (4×50 mL)
  2. dry with materialThe combined organic portions were dried over sodium sulfate
  3. customthe solvents were evaporated under vacuum
  4. customThe solid residue was recrystallized (ethanol-chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-62b5b1e8145b4eb698ed85aabb6b869f
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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