Reaktion #69448

Reaktionsgleichung

NaOH

methyl 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate

HCl

→

8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

Ausbeute 35.8%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 0° C.
2. 2
   EinengenThe solution was partially concentrated
3. 3
   workup.ADDITIONWater was added to the slurry
4. 4
   Extraktionextracted with DCM
5. 5
   WaschenThe organic phase was washed with water
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe formed precipitate was triturated with ether
10. 10
    Filtrationfiltered
11. 11
    Waschenwashed with ether
12. 12
    Sonstigedried under vacuum at 50° C.

Vorschrift

An aqueous NaOH 2N (0.622 mL, 1.24 mmol) solution was added to methyl 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylate (195 mg, 0.41 mmol) in MeOH (2 mL) and the reaction mixture stirred at 40° C. for 6 h. The mixture was cooled to 0° C. and an aqueous HCl 2N (0.684 mL, 1.37 mmol) solution was added dropwise to the reaction mixture until pH ˜5. The solution was partially concentrated and a precipitate appeared. Water was added to the slurry and extracted with DCM. The organic phase was washed with water, dried over MgSO4, filtered and concentrated. The formed precipitate was triturated with ether, filtered, washed with ether, dried under vacuum at 50° C. to afford 8-(1-(3,5-difluorophenyl)pyrrolidin-2-yl)-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (67 mg, 35%) as a pale beige solid. Mass Spectrum: m/z [M+H]+=457.

Quelle