Reaction #56745

Reaction equation

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

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureIt was then heated
2. 2
   Temperatureto reflux under nitrogen for 5 hours
3. 3
   TemperatureUpon cooling
4. 4
   Otherthe solvent was removed
5. 5
   WashThe solution was then washed with water (200 mL) and with aqueous 2N HCl (100 mL)
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated in vacuum

Procedure

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