Hydrochloric Acid → Fingolimod Hydrochloride

Participants

Reaction Steps

To 14.1 g (0.04 mol) of 3-(hydroxymethyl)-3-nitro-1-(p-octylphenyl)butane-1,4-diol in 250 ml of methyl alcohol, 30 ml of concentrated hydrochloric acid was added, followed by the catalyst—10% palladium-carbon. The mixture was stirred at 20 kg/cm2 hydrogen pressure for two days at room temperature. The mixture was then filtered, methyl alcohol was distilled off, the residue was dissolved in water, adjusted to pH 8 with saturated sodium bicarbonate, and extracted with ethyl acetate (100 ml×3). The ethyl acetate extracts were dried over magnesium sulfate, filtered, evaporated. The residue was dissolved in ethanol (50 ml) and a 1N hydrochloric acid (50 ml) was added thereto. The mixture was stirred for 1 h, the solvent was distilled off and the resultant solid were recrystallized from ethanol to give Fingolimod hydrochloride.

Provenance & Evidence