Reacción #44669

Ecuación de reacción

1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]ethanone

methylmagnesium bromide

→

titled compound

2-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]propane-2-ol

Disolventes

tetrahydrofuran

ammonium chloride

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 0° C
2. 2
   OtroThe organic layer was partitioned
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   OtroSolvent was removed by distillation under reduced pressure
6. 6
   Otrothe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate)

Procedimiento

To a solution of 1-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]ethanone (529 mg) in tetrahydrofuran (25 mL) was, under a nitrogen atmosphere, dropwise added methylmagnesium bromide (0.97 M tetrahydrofuran solution, 4.63 mL) at 0° C. The resultant solution was stirred for 1 hour at the same temperature, and then diluted with aqueous ammonium chloride and ethyl acetate. The organic layer was partitioned, washed with brine, and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate), to thereby obtain the titled compound (330 mg). The physical properties of this crude product were as follows.

Fuente