Reaktion #51518

Reaktionsgleichung

5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine

Triethylamine trihydrofluoride

triethylamine

MeOH

→

title compound

Ausbeute 92.5%

2′-O-(dimethylaminooxyethyl)-5-methyluridine

Ausbeute 92.5%

Lösungsmittel

CH2Cl2

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction
2. 2
   SonstigeSolvent removed under vacuum
3. 3
   Wascheneluted with 10% MeOH in CH2Cl2

Vorschrift

Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get the title compound (766 mg, 92.5%). Rf 0.27 (5% MeOH in CH2Cl2). MS (FAB⊕) m/e 346 (M+H⊕)

Quelle