Reaktion #6047

Reaktionsgleichung

[2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanone

methoxylamine hydrochloride

→

title compound

Ausbeute 75.7%

[2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)-cyclobutanone O-methyl oxime

Ausbeute 75.7%

Lösungsmittel

pyridine

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenit was concentrated to approximately 1/4 of the original volume
2. 2
   workup.ADDITIONthen diluted with ethyl acetate
3. 3
   Waschenwashed with saturated aqueous sodium bicarbonate solution
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash chromatography on a 5×38 cm silica gel column
8. 8
   Wascheneluted with 1 L of hexane and 5% acetone in hexane

Vorschrift

A solution of 12.317 g (34.9 mmol) of [2R,3R]-2,3-Bis(((1,1-dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanone, from Step E, in 20 mL of pyridine was added to a solution of 3.160 g (37.8 mmol) of methoxylamine hydrochloride in 80 mL of pyridine. After stirring the reaction mixture for 70 min at ambient temperature, it was concentrated to approximately 1/4 of the original volume then diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on a 5×38 cm silica gel column eluted with 1 L of hexane and 5% acetone in hexane to give 10.228 g (75.7% yield) of the title compound as a mixture of geometrical isomers. .MS DCI-NH3M/Z: 388 (M+H)+.

Quelle