Reacción #1072270

Ecuación de reacción

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

potassium hydroxide

hydrazine hydrate

→

title compound

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe methanol is removed in vacuo
2. 2
   workup.ADDITIONthe reaction mixture is diluted with water
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 (toluene/dioxane/acetic acid: 8/1/1)

Procedimiento

A suspension of 0.27 g (0.53 mmol) (7R,8R,9R)-10-acetyl-3-chloro-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, 0.10 ml (0.60 mmol) aqueous potassium hydroxide (6 N) and 0.20 ml (5.14 mmol) hydrazine hydrate in methanol is stirred at 60° C. for 4 h. The methanol is removed in vacuo and the reaction mixture is diluted with water. 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 (toluene/dioxane/acetic acid: 8/1/1) to provide 0.34 g (0.88 mmol/51%) of the title compound as a colourless solid with a melting point of 123-126° C. (acetone).

Fuente