Reaktion #2070302

Reaktionsgleichung

2,6-dimethylmorpholine

2-(4-fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole

2,6-dimethylmorpholine

→

title compound

Ausbeute 24.0%

rac-(2S,6R)-2,6-Dimethyl-4-{4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-morpholine

Ausbeute 24.0%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder gently reflux for 18 h at 160° C
2. 2
   workup.STIRRINGwas stirred for another 24 h at 160° C
3. 3
   TemperaturAfter cooling to ambient temperature the reaction mixture
4. 4
   Extraktionwas extracted with water (20 mL) and ethyl acetate (20 mL)
5. 5
   ExtraktionThe aqueous layer was extracted with ethyl acetate (20 mL)
6. 6
   Waschenthe combined organic layers were washed with brine (20 mL) and aqueous sodium carbonate (saturated, 20 mL)
7. 7
   TrocknenDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20)

Vorschrift

A suspension of 2-(4-fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (200 mg, 0.62 mmol) in 2,6-dimethylmorpholine (2.00 mL, 16.0 mmol) was heated for 30 min at 200° C. (microwave) followed by stirring under gently reflux for 18 h at 160° C. After addition of DMSO (2 mL) and 2,6-dimethylmorpholine (0.50 mL, 4.00 mmol) the solution was stirred for another 24 h at 160° C. After cooling to ambient temperature the reaction mixture was extracted with water (20 mL) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (20 mL) and the combined organic layers were washed with brine (20 mL) and aqueous sodium carbonate (saturated, 20 mL). Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=70:10:20 to 40:40:20) afforded the title compound (61 mg, 24%) as a white solid. MS: m/e=417.3 [M+H]+.

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