反応 #365377

反応方程式

HCl

4-acetyl-1-(t-butoxycarbonyl)piperidine

methyl phenylacetate

sodium hydride

→

title compound

収率 65.7%

1-(1-(t-Butoxycarbonyl)piperidin-4-yl)-4-phenylbutane-1,3-dione

収率 65.7%

溶媒

ether

THF

THF

反応条件

後処理

1. 1
   その他The layers were separated
2. 2
   抽出the aqueous layer was extracted three times with ether
3. 3
   洗浄The combined organic layers were washed with brine (150 mL)
4. 4
   乾燥dried over sodium sulfate
5. 5
   濃縮concentrated
6. 6
   その他The crude product was purified by FC (20% ethyl acetate in hexanes)

実験手順

To a suspension of 60% sodium hydride (1.07 g) in THF (15 mL) at 0° C. was added a solution of 4-acetyl-1-(t-butoxycarbonyl)piperidine from Step B2 (3.03 g, 13.3 mmol) and methyl phenylacetate (6.01 g, 39.9 mmol) in THF (6 mL) over 20 min. The reaction was stirred for another 4 h as it was allowed to warm to rt. The mixture was diluted with ether (30 mL) and poured into 1N HCl. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic layers were washed with brine (150 mL), dried over sodium sulfate and concentrated. The crude product was purified by FC (20% ethyl acetate in hexanes) to give the title compound (3.02 g). Rf: 0.30 (20% ethyl acetate in hexane). The 1H NMR data was the same as that obtained from the product of Method A.

出典