反応 #8861

反応方程式

tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

tert-Butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

Jones reagent

→

title compound

収率 66.7%

tert-Butyl 1-(1-oxoprop-1-yl)-2-oxo-8-azaspiro[4.5]decane-8-carboxylate

収率 66.7%

溶媒

acetone

反応条件

後処理

1. 1
   その他was then quenched with isopropanol
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   抽出extracted three times with methylene chloride
4. 4
   洗浄The combined organic layers were washed with brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The residue was purified by flash chromatography
9. 9
   洗浄eluting with 20% ethyl acetate in hexanes

実験手順

To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.050 g, 0.16 mmol) from Step E in acetone (2 mL) at 0° C. was added 2.6M Jones reagent (0.122 mL, 0.32 mmol). The reaction was stirred at room temperature for 10 min and was then quenched with isopropanol. The mixture was diluted with water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to afford the title compound (0.033 g).

出典