反応 #8868

反応方程式

tert-butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

tert-Butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Dess-Martin reagent

→

title product

収率 69.5%

tert-Butyl 4-(4-phenyl-1,3-dioxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

収率 69.5%

溶媒

ether

methylene chloride

反応条件

後処理

1. 1
   その他quenched with 1N sodium hydroxide
2. 2
   workup.ADDITIONthe mixture was diluted with water
3. 3
   抽出extracted twice with ether
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 (10% ethyl acetate in hexanes)

実験手順

To a solution of tert-butyl 4-(4-phenyl-3-hydroxy-1-oxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (494 mg, 0.98 mmol) from Step F in methylene chloride (10 mL) at room temperature was added Dess-Martin reagent (621 mg, 1.5 mmol). After 3 h, the reaction was diluted with ether and quenched with 1N sodium hydroxide. After stirring for 30 min, the mixture was diluted with water and extracted twice with ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexanes) to afford the title product (343 mg).

出典