Reacción #365377

Ecuación de reacción

HCl

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

methyl phenylacetate

sodium hydride

→

title compound

Rendimiento 65.7%

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

Rendimiento 65.7%

Disolventes

ether

THF

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente