Reaktion #365377

Reaktionsgleichung

HCl

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

methyl phenylacetate

sodium hydride

→

title compound

Ausbeute 65.7%

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

Ausbeute 65.7%

Lösungsmittel

ether

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted three times with ether
3. 3
   WaschenThe combined organic layers were washed with brine (150 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe crude product was purified by FC (20% ethyl acetate in hexanes)

Vorschrift

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.

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