Reaktion #60324

Reaktionsgleichung

6-hydroxy-1-tetralone

N,N-dimethylethanolamine

PPh3

DEAD

→

6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Lösungsmittel

Ether

Reaktionsbedingungen

Vorschrift

Ether linked analogs such as 45, are prepared by the convergent synthesis depicted in scheme 13. The 6-hydroxy-1-tetralone 14 is reacted with an amine, such as N,N-dimethylethanolamine, preferably in the presence of PPh3 and DEAD at a temperature preferably between about 0° C. and about RT to form the 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 42. the 6-(2-dimethylamino-ethoxy)-3,4-dihydro-2H-naphthalen-1-one 42 is reacted with hydroxylamine hydrochloride and base, such as Et3N. The reaction is heated above RT, preferably at reflux to form the oxime 43. Hydrogenation of the oxime 43, such as with Pd/C and H2 provides the amine 44 which can be coupled with the appropriate acid to form the desired compound 45.

Quelle