Water → 1-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthine

HRID 361487

Reaktionsgleichung

Reaktionsgleichung von HRID 361487
[CH2:1]([N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].C[N+]1([O-])CC[O:26]CC1.[OH2:30].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:30][CH:7]([CH2:8][OH:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:9]1[C:18](=[O:19])[C:17]2[N:16]([CH3:20])[CH:15]=[N:14][C:13]=2[N:12]([CH3:21])[C:10]1=[O:11]

Komponenten

8

Edukt 4

HCID 962Water2×HCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 152306341-(7-Octenyl)-3,7-dimethylxanthine

Produkt 1

HCID 97973341-(7,8-Dihydroxyoctyl)-3,7-dimethylxanthineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6386tert-ButanolKatalysatorHCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of 1-(7-octenyl)-3,7-dimethylxanthine (1.00 g, 4.5 mmol), 4-methylmorpholine-N oxide (553 mg, 4.7 mmol), and a 2.5% solution of osmium tetroxide in t-butanol (3 drops) in acetone (25 mL) and water (20 mL) was stirred for 4 days. After addition of a saturated aqueous solution of sodium hydrosulfite (10 mL) and 30 minutes of continued stirring, the reaction mixture was added to water (50 mL) and extracted with 20% ethanol/dichloromethane (3×50 mL). Evaporation of the solvent under vacuum yielded an off-white residue. The residue was recrystallized in ethanol, yielding 726 mg (63% yield) 1-(7,8-dihydroxyoctyl)-3,7-dimethylxanthine (inventive compound no. 1538) as a white solid.

Aufarbeitung

  1. extractionextracted with 20% ethanol/dichloromethane (3×50 mL)
  2. customEvaporation of the solvent under vacuum
  3. customyielded an off-white residue
  4. customThe residue was recrystallized in ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8591e9325b1349d9b3571fe26e232a37
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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