Hydrochloric Acid → (S)-4,4-Dimethylpyrrolidin-3-OL hydrochloride

To a solution of (3S)-4,4-dimethyl-1-(phenylmethyl)-3-pyrrolidinol (J. Med. Chem. 1992, 35, 4205-4213) (0.7738 g, 3.769 mmol) in MeOH (38 mL) was added 1 N aq. HCl (3.8 mL, 3.8 mmol) and 10% Pd/C (50% water, 230 mg). The mixture was hydrogenated under balloon pressure for 18 h, and was then filtered through a 0.2 μm filter tip syringe. The resulting solution was concentrated in vacuo and azeotroped with MeOH (2×50 mL) to afford (3S)-4,4-dimethyl-3-pyrrolidinol hydrochloride (0.5267 g, 93% yield) as a light orange solid. LCMS: (M+H)+: 116.1.