Hydrochloric Acid → [(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

A mixture of crude (2S)-2[(benzyloxy)methyl-2,3-dihydro[1,4]dioxino[2,3-f]-quinoline product mixture (57.6 g, 0.179 mol) from example 7 in toluene (300 mL) was mixed with 20% HCl (436 g, 3.59 mol) and heated at 80° C. After 30 min, the reaction mixture was cooled to room temperature. The two layers were separated. A 30% NH4OH solution (400 mL) was added to the aqueous layer at 10–20° C. to pH 10. This was stirred for 30 min, the solid was filtered, washed with water and recrystallized from CH3OH (200 mL) to give 25.7 g (61.9%) of the title alcohol as an off-white solid.

Provenance & Evidence