Reacción #56745

Ecuación de reacción

hydroxylamine hydrochloride

ethanol pyridine

1-[(3S)-5-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone

→

title compound

1-[5-Hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone oxime

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaIt was then heated
2. 2
   Temperaturato reflux under nitrogen for 5 hours
3. 3
   TemperaturaUpon cooling
4. 4
   Otrothe solvent was removed
5. 5
   LavadoThe solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuum

Procedimiento

A solution of hydroxylamine hydrochloride (2.38 g, 34.2 mmole) in 1:1 ethanol/pyridine (100 mL) was added to a solution of 1-[(3S)-5-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-1-ethanone (1.92 g, 8.57 mmole) in ethanol (200 mL). It was then heated to reflux under nitrogen for 5 hours. Upon cooling, the solvent was removed and replaced with ethyl acetate. The solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuum to give 1.89 g (93%) of the (S)-enantiomer of the title compound as a gray solid, m.p. 162° C., MS (ESI) m/z 240 (M+H)+.

Fuente