Reaktion #45647

Reaktionsgleichung

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Ausbeute 93.3%

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 93.3%

Lösungsmittel

brine

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   SonstigeThe aqueous layer was separated
3. 3
   Extraktionthis was extracted twice with ethyl acetate
4. 4
   Waschenthis was washed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeThe insoluble matter was separated by filtration
7. 7
   Sonstigethe solvent was evaporated away
8. 8
   Sonstigethe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

Vorschrift

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-112) (35 mg, 0.11 mmol) was dissolved in anhydrous dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (24 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (22 μl, 0.17 mmol) were added. This mixture liquid was stirred at 90° C. for 12 hours, then cooled to room temperature. This was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, this was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (41.5 mg, 91%) as a white solid. This was further recrystallized from hexane/diethyl ether to obtain a cream powder (27.5 mg).

Quelle