反応 #8867

反応方程式

ammonium chloride

phenylacetaldehyde

tert-butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

HMPA

LHMDS

→

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

溶媒

ether

THF

THF

THF

反応条件

後処理

1. 1
   抽出extracted three times with ether
2. 2
   洗浄The combined organic layers were washed with brine
3. 3
   乾燥dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by flash chromatography (10 to 30% ethyl acetate in hexanes)
7. 7
   その他to afford
8. 8
   その他recovered

実験手順

To a solution of tert-butyl 4-acetyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (4.6 g, 12 mmol) in THF (120 mL) at −70° C. was added HMPA (20.7 mL, 120 mmol) and 1M LHMDS in THF (12 mL, 12 mmol). After 1 h, phenylacetaldehyde (5.7 g, 48 mmol) was added in THF (80 mL) over 10 min and the reaction was stirred for 1 h. The mixture was then poured into ether and aq. ammonium chloride solution and extracted three times 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 to 30% ethyl acetate in hexanes) to afford recovered starting material (2.15 g) and the title product (2.2 g).

出典