Reaktion #68077

Reaktionsgleichung

ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

sodium hydroxide

sodium hydroxide

→

1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid

Ausbeute 22.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturrefluxed
3. 3
   Temperaturwith heating for 2 hours
4. 4
   Temperaturrefluxed
5. 5
   Temperaturwith heating for 5 hours
6. 6
   workup.WAITAfter left
7. 7
   Sonstigethe solvent was removed under reduced pressure, water
8. 8
   workup.ADDITIONwas added
9. 9
   SonstigeThe solvent was removed under reduced pressure
10. 10
    Sonstigethe residue thus obtained
11. 11
    Sonstigewas purified by reversed-phase silica gel column chromatography [eluent; acetonitrile: water=3: 7]

Vorschrift

To 1 mL of an ethanol solution containing 0.10 g of ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 0.15 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 2 hours. Then, more 0.10 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 5 hours. After left to stand at room temperature overnight, the solvent was removed under reduced pressure, water was added, and adjusted to pH 6.7 with 6.0 mol/L hydrochloric acid. The solvent was removed under reduced pressure, and the residue thus obtained was purified by reversed-phase silica gel column chromatography [eluent; acetonitrile: water=3: 7] to give 21 mg of 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid as a white solid.

Quelle