반응 #168740

반응 방정식

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

용매

tert-butanol

tert-butanol

반응 조건

후처리

1. 1
   기타was removed under reduced pressure
2. 2
   추출The product was extracted with ethyl acetate from the remaining aqueous phase
3. 3
   세척The organic phases were washed with water and brine
4. 4
   건조dried over Na2SO4
5. 5
   기타Volatiles were removed under reduced pressure
6. 6
   기타The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

실험 절차

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)+].

출처