Reaktion #89721

Reaktionsgleichung

dimethyl(2S,3S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

tetrahydrofuran

3-fluoro-phenol

triphenylphosphine

diethyl azodicarboxylate

→

dimethyl(2S,3S,5S)-5-(3-fluorophenoxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter concentrated
2. 2
   Sonstigeto dry
3. 3
   Sonstigethe mixture was purified on silica gel
4. 4
   Wascheneluting with 0 to 40% EtOAc in hexane

Vorschrift

To a solution of dimethyl(2S,3S,5R)-5-hydroxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (50.0 mg, 0.000123 mol) in tetrahydrofuran (0.50 mL, 0.00617 mol) was added 3-fluoro-phenol (0.0134 mL, 0.000148 mol), triphenylphosphine (38.8 mg, 0.000148 mol), followed by diethyl azodicarboxylate (0.0233 mL, 0.000148 mol). The mixture was heated at 70 Celsius overnight. After concentrated to dry, the mixture was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to generate the phenyl ether compound (27 mg, 44%). MS (ESI): (M+H)+=500.05.

Quelle