Reacción #1072275

Ecuación de reacción

(7R,8R,9R)-10-acetyl-3-hydroxymethyl-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

potassium carbonate

→

title compound

(7R,8R,9R)-3-Hydroxymethyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Disolventes

aminoethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction is quenched
2. 2
   workup.ADDITIONby adding of saturated aqueous ammonium chloride solution
3. 3
   ExtracciónSubsequently the mixture is extracted twice with dichloromethane
4. 4
   LavadoThe combined organic layers are washed with brine
5. 5
   Secadodried over sodium sulphate
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe crude product is purified by column chromatography (dichloromethane/methanol: 13/1)

Procedimiento

A suspension of 0.60 g (1.10 mmol) of (7R,8R,9R)-10-acetyl-3-hydroxymethyl-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine and 0.30 g (2.10 mmol) potassium carbonate in aminoethanol is stirred at 90° C. for 2 h. The reaction is quenched by adding of saturated aqueous ammonium chloride solution. Subsequently the mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (dichloromethane/methanol: 13/1) to give 0.20 g (0.52 mmol/47%) of the title compound as a colourless solid with a melting point of 180-183° C. (diethyl ether).

Fuente