Reacción #44986

Ecuación de reacción

Methyl trans-4-[{2-[(t-butoxycarbonyl)amino]ethyl}-(chloroacetyl)amino]cyclohexanecarboxylate

sodium hydride

ammonium chloride

water

→

t-butyl 4-[trans-4-(methoxycarbonyl)cyclohexyl]-3-oxopiperazine-1-carboxylate

Rendimiento 59.7%

Disolventes

N,N-dimethylacetamide

—

oil

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder ice-cooling
2. 2
   Temperaturasame cooling conditions
3. 3
   Temperaturacooling
4. 4
   Extracciónthe mixture is extracted with ethyl acetate
5. 5
   LavadoThe organic layer is washed with water and saturated brine successively
6. 6
   Secadodried over sodium sulfate
7. 7
   Otroevaporated
8. 8
   Otroto remove the solvent under reduced pressure
9. 9
   OtroThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Procedimiento

Methyl trans-4-[{2-[(t-butoxycarbonyl)amino]ethyl}-(chloroacetyl)amino]cyclohexanecarboxylate (560 mg) obtained in Reference Example 71(2) is dissolved in N,N-dimethylacetamide (5 ml), and 60% sodium hydride in oil (119 mg) is added thereto under ice-cooling. The reaction solution is then stirred for 0.5 hours under the same cooling conditions. Saturated aqueous ammonium chloride solution and water are poured to the reaction solution successively under ice-cooling, and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to give t-butyl 4-[trans-4-(methoxycarbonyl)cyclohexyl]-3-oxopiperazine-1-carboxylate (302 mg).

Fuente