Reacción #44627

Ecuación de reacción

dichloromethane

(E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylic acid methyl ester

→

title compound

Rendimiento 26.3%

(4R,9aS)-4-(3,4,5-trifluorophenyl)-3,4,7,9a-tetrahydro-1H-pyrido[2,1-c][1,4]oxazin-6-one

Rendimiento 26.3%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction solution
2. 2
   Temperaturawas heated
3. 3
   Temperaturaunder reflux for 1.5 hr in nitrogen atmosphere
4. 4
   OtroThe resulting reaction solution
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Procedimiento

Grubbs catalyst second generation (285 mg) was added to a dichloromethane solution (100 mL) of (E)-3-[(3S,5R)-4-(3-butenoyl)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]acrylic acid methyl ester (1.24 g). The resulting reaction solution was heated under reflux for 1.5 hr in nitrogen atmosphere. The reaction solution was cooled to room temperature, and triethylamine (3 mL) was added thereto. The resulting reaction solution was stirred for 10 min and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 250 mg of the title compound. The physical property values of this compound were as follows:

Fuente