Reacción #92315

Ecuación de reacción

citric acid

(1S,4S,5S)-4-bromo-6-oxabicyclo[3.2.1]octan-7-one

dimethylamine

→

title compound

Rendimiento 90.0%

(1S,3S,4S)-3-Hydroxy-4-bromo-N,N-dimethylcyclohexanecarboxamide

Rendimiento 90.0%

Disolventes

ethyl acetate

Ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe obtained mixture was then stirred for 30 minutes, so that the organic layer
2. 2
   Otrowas separated
3. 3
   ExtracciónFurther, the aqueous layer was extracted with ethyl acetate (1875 ml)
4. 4
   Concentraciónthe gathered organic layer was then concentrated to 1250 ml
5. 5
   workup.ADDITIONThereafter, water (500 ml) was added to the concentrated solution
6. 6
   Concentraciónthe mixed solution was then concentrated again

Procedimiento

Ethyl acetate (1250 ml) was cooled to 5° C., and (1S,4S,5S)-4-bromo-6-oxabicyclo[3.2.1]octan-7-one (250 g) was then added thereto. Thereafter, a 50% dimethylamine aqueous solution (382 ml) was added to the above obtained solution, and the obtained mixture was then stirred for 14 hours. Thereafter, citric acid (234.2 g), 20% saline (500 ml), and ethyl acetate (625 ml) were added to the reaction mixture, and the obtained mixture was then stirred for 30 minutes, so that the organic layer was separated. Further, the aqueous layer was extracted with ethyl acetate (1875 ml). The organic layers were gathered, and the gathered organic layer was then concentrated to 1250 ml. Thereafter, water (500 ml) was added to the concentrated solution, and the mixed solution was then concentrated again to obtain the title compound (274.5 g, yield: 90%) in the form of an aqueous solution (625 ml).

Fuente