Reaktion #73060

Reaktionsgleichung

hydrochloric acid

tert-Butyl {4-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydropyran-4-yl}carbamate

tetrahydro-4H-pyran-4-one

cyclohexanone

→

4-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydropyran-4-amine

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Temperaturwas heated
3. 3
   Temperaturat reflux for 4 hours
4. 4
   Einengenwas then concentrated under reduced pressure
5. 5
   SonstigeA solid was isolated by filtration

Vorschrift

Under a nitrogen atmosphere, a mixture of tert-Butyl {4-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydropyran-4-yl}carbamate (3.0 g, prepared according to the general methods of Parts A through F of Example 54 using tetrahydro-4H-pyran-4-one in lieu of cyclohexanone in Part A), hydrochloric acid (12.2 mL of 2.8 M in ethanol), and ethanol (18 mL) was heated at reflux for 4 hours. The reaction mixture was allowed to cool to ambient temperature and was then concentrated under reduced pressure. The residue was combined with isopropanol (100 mL). A solid was isolated by filtration to provide 2.56 g of 4-[(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]tetrahydropyran-4-amine as a tan solid.

Quelle