反応 #6047

反応方程式

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

methoxylamine hydrochloride

→

title compound

収率 75.7%

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

収率 75.7%

溶媒

pyridine

pyridine

反応条件

後処理

1. 1
   濃縮it was concentrated to approximately 1/4 of the original volume
2. 2
   workup.ADDITIONthen diluted with ethyl acetate
3. 3
   洗浄washed with saturated aqueous sodium bicarbonate solution
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by flash chromatography on a 5×38 cm silica gel column
8. 8
   洗浄eluted with 1 L of hexane and 5% acetone in hexane

実験手順

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)+.

出典