Reaction #168740

Reaction equation

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

Solvents

tert-butanol

tert-butanol

Conditions

Workup

1. 1
   Otherwas removed under reduced pressure
2. 2
   ExtractionThe product was extracted with ethyl acetate from the remaining aqueous phase
3. 3
   WashThe organic phases were washed with water and brine
4. 4
   Dryingdried over Na2SO4
5. 5
   OtherVolatiles were removed under reduced pressure
6. 6
   OtherThe crude product was purified by automated column chromatography (cyclohexane/ethyl acetate)

Procedure

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)+].

Source