Réaction #56745

Équation de réaction

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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureIt was then heated
2. 2
   Températureto reflux under nitrogen for 5 hours
3. 3
   TempératureUpon cooling
4. 4
   Autrethe solvent was removed
5. 5
   LavageThe solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated in vacuum

Mode opératoire

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)+.

Source