Hydrochloric Acid → (2S)-2-amino-2-(pyridin-3-yl)ethan-1-ol dihydrochloride

Participants

Reaction Steps

A mixture of (S)—N—((S)-2-(tert-butyldimethylsilyloxy)-1-(pyridin-3-yl)ethyl)-2-methylpropane-2-sulfinamide (0.2 g, 1.77 mmol) in MeOH (9 mL) was treated with 4N hydrogen chloride (2.21 mL, 8.85 mmol) at 0° C. The mixture was allowed to warm up to ambient temperature and stirred for 1 hour. The mixture was concentrated and the residue treated with aqueous saturated NaHCO3/EtOAc. The organic layer was dried (phase separator silicone treated filter paper), concentrated. The residue was purified on silica gel (2-10% 7N ammonia in MeOH in DCM) to provide (S)-2-amino-2-(pyridin-3-yl)ethanol dihydrochloride (0.060 g, 16% yield) as a beige solid.

Provenance & Evidence