反応 #168740

反応方程式

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

溶媒

tert-butanol

tert-butanol

反応条件

後処理

1. 1
   その他was removed under reduced pressure
2. 2
   抽出The product was extracted with ethyl acetate from the remaining aqueous phase
3. 3
   洗浄The organic phases were washed with water and brine
4. 4
   乾燥dried over Na2SO4
5. 5
   その他Volatiles were removed under reduced pressure
6. 6
   その他The crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

実験手順

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)+].

出典