Reaction #44627

Reaction equation

dichloromethane

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

→

title compound

Yield 26.3%

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

Yield 26.3%

Solvents

triethylamine

Conditions

Workup

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

Procedure

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:

Source