Reaktion #45626

Reaktionsgleichung

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

2-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Ausbeute 52.0%

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

Ausbeute 52.0%

Lösungsmittel

water

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   WaschenThe organic layer was washed with saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   SonstigeThe solvent was evaporated away
5. 5
   Wascheneluted with a mixed solvent of chloroform/methanol (10:1

Vorschrift

2-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-90) (70 mg, 0.19 mmol) was dissolved in dimethyl sulfoxide (1.4 ml), triethylamine (63 μl, 0.45 mmol) and (3S)-3-(dimethylamino)pyrrolidine (29 μl, 0.23 mmol) were added, followed by stirring at 90° C. for 4 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to preparative, thin-layer silica gel column, chromatography, eluted with a mixed solvent of chloroform/methanol (10:1, v/v) to obtain the entitled compound (46 mg, 52%) as a yellow oily substance.

Quelle