Reacción #569877

Ecuación de reacción

6-fluorospiro[chroman-4,4'-imidazolidine]2,2',5'-trione

hydrochloric acid

diisobutylaluminum hydride

diisobutylaluminum hydride

toluene

→

desired compound

2-Hydroxy-6-fluorospiro[chroman-4,4'-imidazolidine]2',5'-dione

Disolventes

hexane

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to 0° C.
2. 2
   workup.STIRRINGwas stirred for 24 hours
3. 3
   Otrowas recooled to -40° C.
4. 4
   Temperaturathe reaction warmed to 0° C
5. 5
   Extracciónthe mixture extracted with ethyl acetate
6. 6
   LavadoThe combined extracts were washed
7. 7
   Otrodried
8. 8
   Concentraciónconcentrated to dryness
9. 9
   OtroThe residue was chromatographed
10. 10
    Otroto give 67 mg

Procedimiento

To a slurry of 640 mg. (0.002 mole) of 6-fluorospiro[chroman-4,4'-imidazolidine]2,2',5'-trione in 40 ml. of toluene at -78° C. was added 852 mg. (0.006 mole) of diisobutylaluminum hydride in hexane, and the reaction mixture allowed to stir at -78° C. for 30 minutes. The reaction was allowed to warm to 0° C. and was stirred for 24 hours. The reaction was recooled to -40° C., 6 ml. of dry tetrahydrofuran was added and the reaction warmed to 0° C. Additional diisobutylaluminum hydride (1.0 ml) was added in 0.2 ml. portions. The reaction mixture was added to 10% hydrochloric acid and the mixture extracted with ethyl acetate. The combined extracts were washed dried and concentrated to dryness. The residue was chromatographed to give 67 mg. of the desired compound, m.p. 247°-251° C. (dec.).

Fuente