Reaktion #44634

Reaktionsgleichung

potassium carbonate

methanol

THF

4-nitrobenzoic acid (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl ester

→

title compound

Ausbeute 95.1%

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

Ausbeute 95.1%

Lösungsmittel

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction solution
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with saturated saline twice
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   workup.ADDITIONTo the obtained residue, diethylether was added
7. 7
   SonstigeThe insoluble matter was removed by filtration
8. 8
   Einengenthe filtrate was concentrated
9. 9
   SonstigeThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1)

Vorschrift

A potassium carbonate powder (6.43 g) was added to a solution mixture of methanol (90 mL) and THF (10 mL) of 4-nitrobenzoic acid (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl ester (7.03 g). The resulting reaction solution was stirred at room temperature for 1 hr, and ethyl acetate and water were added thereto. The organic layer was separated, washed with saturated saline twice, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue, diethylether was added. The insoluble matter was removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to give 4.49 g of the title compound. The physical property values of this compound were as follows:

Quelle