Reacción #8254

Ecuación de reacción

sodium bicarbonate

5-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzene

n-butyllithium

(R)-glycidylbutyrate

→

title product

Rendimiento 33.7%

3-(3-Fluoro-4-(4-methylimidazol-1-yl)phenyl)-5(R)-hydroxymethyloxazolidin-2-one

Rendimiento 33.7%

Disolventes

ethyl acetate

tetrahydrofuran

1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to −70°
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for 16 hours
4. 4
   Otrowas removed
5. 5
   Lavadowashed well with diethyl ether

Procedimiento

5-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 114 ml), over 30 minutes. After stirring for 30 minutes at 25–70°, a solution of (R)-glycidylbutyrate (26.35 g, 0.183 M) in dry tetrahydrofuran (50 ml) was added over 15 minutes. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated with aqueous sodium bicarbonate (5%, 500 ml) and ethyl acetate (800 ml), and undissolved solid was removed and washed well with diethyl ether to give title product (16.3 g).

Fuente