Reaktion #2276319

Reaktionsgleichung

8-[2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-phenyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-ol

sodium bicarbonate

→

title compound

6-Chloro-6′,7′-dihydro-3H,5′H-spiro[2-benzofuran-1,8′-imidazo[1,5-a]pyridine]

Lösungsmittel

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Extraktionextracted with dichloromethane (3×140 ml)
3. 3
   TrocknenThe combined organic phases are dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resulting residue is purified by flash chromatography (SiO2 60 F)

Vorschrift

A suspension of 2.672 mmol of 8-[2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-phenyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-ol in 40 ml of 1N aqueous HCl is stirred at 95° C. for 40 hours, then cooled to room temperature. The mixture is basified to pH 12 by dropwise addition of aqueous saturated sodium bicarbonate solution, and then extracted with dichloromethane (3×140 ml). The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a beige solid. Rf=0.14 (EtOAc-methanol 10:1); Rt=3.04 (gradient I).

Quelle