반응 #44635

반응 방정식

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

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   기타The resulting reaction solution
2. 2
   기타The organic layer was separated
3. 3
   세척washed with 1 N hydrochloric acid, water
4. 4
   건조Then, the organic layer was dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (hexane:diethyleter=49:1 to 19:1)

실험 절차

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). The resulting reaction solution was stirred at room temperature for 3 hr, and ethyl acetate and water were added thereto. The organic layer was separated and washed with 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. Then, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:diethyleter=49:1 to 19:1) to give 684 mg of the title compound. The physical property values of this compound were as follows:

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