Reaktionsgleichung
C1(C[O:8][C@@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[NH:14][C:15]2[N:23]=[CH:22][N:21]=[C:20]3[C:16]=2[N:17]=[CH:18][N:19]3[CH:24]2[C@H:28]([OH:29])[C@H:27]([OH:30])[C@@H:26]([CH2:31][Cl:32])[O:25]2)C=CC=CC=1>C(O)C.C1CCCCC1.[OH-].[Pd+2].[OH-]>[OH:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[NH:14][C:15]1[N:23]=[CH:22][N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH:24]1[C@H:28]([OH:29])[C@H:27]([OH:30])[C@@H:26]([CH2:31][Cl:32])[O:25]1Komponenten
5
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
The 2-(6-{[(1R,2R)-2-(phenylmethoxy)cyclopentyl]amino}purin-9-yl)(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol obtained in Example 11 (22 g) was dissolved in ethanol (450 mL) and cyclohexane (200 mL). To this solution was added palladium hydroxide (20 mole %, 1 gram added initially, 1 gram after 6 hours, and 1 gram after 14 hours), and the reaction mixture was refluxed for 18 hours. The reaction mixture was filtered thru celite while still hot, and solvent removed from the filtrate under reduced pressure. The product was triturated with ethanol (20 mL), filtered, and washed with ethanol, to afford 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol as a white powder).
Aufarbeitung
- additionadded initially
- temperature1 gram after 14 hours), and the reaction mixture was refluxed for 18 hours
- filtrationThe reaction mixture was filtered thru celite while still hot, and solvent
- customremoved from the filtrate under reduced pressure
- customThe product was triturated with ethanol (20 mL)
- filtrationfiltered
- washwashed with ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-b50a3d9def8b4ebf91809c21f83afba4
- Quelldatensatz
- uspto-grants-2011_05
- Patentnummer
- US07939509B2
Verknüpfte Notizen
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