Reacción #168740

Ecuación de reacción

water

N—[(R)-1-(3-Bromo-5-nitro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide

KOtBu

→

title compound

(R)-5-(3-Bromo-5-nitro-phenyl)-6-methyl-morpholin-3-one

Disolventes

tert-butanol

tert-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed under reduced pressure
2. 2
   ExtracciónThe product was extracted with ethyl acetate from the remaining aqueous phase
3. 3
   LavadoThe organic phases were washed with water and brine
4. 4
   Secadodried over Na2SO4
5. 5
   OtroVolatiles were removed under reduced pressure
6. 6
   OtroThe crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

Procedimiento

N—[(R)-1-(3-Bromo-5-nitro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (4.45 g, 10.76 mmol) and KOtBu (2.414 g, 21.52 g) were suspended in 55 ml tert-butanol under N2 and heated 100° C. for 30 min. After completion water was added to the reaction and tert-butanol was removed under reduced pressure. The product was extracted with ethyl acetate from the remaining aqueous phase. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure. The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate) yielding the title compound as tan solid. 1H-NMR (360 MHz, DMSO-d6): 8.88 (1H, NH), 8.35 (s, 1H), 8.28 (s, 1H), 8.14 (s, 1H), 4.16 (m, 1H), 4.06 (s, 2H), 3.74 (m, 1H), 1.50 (s, 3H); MS: 316 [(M+H)+].

Fuente