تفاعل #8250

معادلة التفاعل

sodium bicarbonate

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

n-butyllithium

(R)glycidylbutyrate

→

title compound

المردود 44.5%

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

المردود 44.5%

المذيبات

ethyl acetate

tetrahydrofuran

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

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to −70°
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for 16 hours
4. 4
   أخرىthe organic layer separated
5. 5
   استخلاصthe aqueous extracted with further ethyl acetate (3×750 ml)
6. 6
   تجفيفThe combined extracts were dried (magnesium sulfate)
7. 7
   أخرىevaporated
8. 8
   أخرىthe resulting oil triturated with diethyl ether

الإجراء التجريبي

5-Benzyloxycarbonylamino-2-(2-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 −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), the organic layer separated, and the aqueous extracted with further ethyl acetate (3×750 ml). The combined extracts were dried (magnesium sulfate) and evaporated, and the resulting oil triturated with diethyl ether. The resulting solid was recrystallisd from isopropanol to give the title compound (21.5 g).

المصدر