Reaktion #69465

Reaktionsgleichung

NaOH

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

HCl

→

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

Ausbeute 83.2%

Lösungsmittel

MeOH

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 0° C.
2. 2
   EinengenAfter dilution with water (9 mL), the reaction mixture was concentrated to half volume
3. 3
   ExtraktionThe aqueous phase was extracted with DCM
4. 4
   Einengenthe organic phase was concentrated to dryness
5. 5
   Sonstigewas triturated in EtAc
6. 6
   Filtrationcollected by filtration
7. 7
   Waschenwashed with EtAc, diethyl ether
8. 8
   Sonstigedried under vacuum at 50° C.

Vorschrift

An aqueous NaOH 2N (2.55 ml, 5.10 mmol) solution was added to methyl 8-[(2R)-1-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-4-oxo-chromene-6-carboxylate (0.79 g, 1.68 mmol) in a mixture of MeOH (9 mL) and DCM (6 mL) and the reaction mixture was stirred at room temperature overnight. The mixture was cooled to 0° C. and an aqueous HCl 2N (2.5 mL, 5.0 mmol) solution was added dropwise to the reaction mixture until pH ˜3. After dilution with water (9 mL), the reaction mixture was concentrated to half volume. The aqueous phase was extracted with DCM, the organic phase was concentrated to dryness, leading to a foam, which was triturated in EtAc, collected by filtration, washed with EtAc, diethyl ether, dried under vacuum at 50° C. to afford 8-[(2R)-1-(3,5-difluorophenyl)pyrrolidin-2-yl]-2-morpholino-4-oxo-chromene-6-carboxylic acid (0.638 g, 83%) as an off-white solid. Mass Spectrum: m/z [M+H]+=457.

Quelle