Reacción #44607

Ecuación de reacción

tert-butyldiphenylsilyl chloride

DMF

[(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]-carbamic acid tert-butyl ester

imidazole

→

title compound

[(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamic acid tert-butyl ester

Disolventes

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic layer was separated
2. 2
   Lavadowashed with 1 N hydrochloric acid, water
3. 3
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (eluting solvent: hexane:diethylether=49:1 to 19:1)

Procedimiento

In nitrogen atmosphere, tert-butyldiphenylsilyl chloride (2.0 mL) was added dividedly four times to a DMF solution (3 mL) of [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]-carbamic acid tert-butyl ester (610 mg) and imidazole (817 mg). This reaction solution was stirred at room temperature for 3 hr. To the reaction solution, ethyl acetate and water were added. The organic layer was separated, washed with 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane:diethylether=49:1 to 19:1) to give 684 mg of the title compound. The physical property values of this compound were as follows:

Fuente