2-Chloroadenosine → 2-[2-(1,4-Dioxaspiro[4.5]dec-8-yl)ethylamino]adenosine
Reaktionsgleichung
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[O:21]1[C:25]2([CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][NH2:33])[CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1>>[O:21]1[C:25]2([CH2:30][CH2:29][CH:28]([CH2:31][CH2:32][NH:33][C:2]3[N:3]=[C:4]([NH2:20])[C:5]4[N:6]=[CH:7][N:8]([C:18]=4[N:19]=3)[C@@H:9]3[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]3[OH:11])[CH2:27][CH2:26]2)[O:24][CH2:23][CH2:22]1Komponenten
3
Versuchsvorschrift
A mixture of 2-chloroadenosine (0.3 g) and 1,4-dioxaspiro[4.5]decane-8-ethanamine (1.0 g) is heated under nitrogen at 140° for 6 hours. It is evaporated to dryness at reduced pressure, the residue is dissolved in ethanol, the solution is treated with propylene oxide (2 ml) and stirred 4 hours. The precipitate is collected, washed with ethanol and dried in vacuo to give 2-[2-(1,4-dioxaspiro[4.5]dec-8-yl)ethylamino]adenosine, [alpha]D25 =-27.3° (MeOH), m.p. 133°-137°.
Aufarbeitung
- temperatureis heated under nitrogen at 140° for 6 hours
- customIt is evaporated to dryness at reduced pressure