Hydrochloric Acid → (S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

Route A: To a solution of [1 (S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]carbamic acid tert-butyl ester (Preparation 19, 11.6 g, 31.7 mmol) in methanol (40 mL) was added hydrochloric acid in dioxane (24 mL, 4N, 95.0 mmol) and the reaction mixture stirred at rt for 6 h. The solvent was removed in vacuo and the residue was dissolved in water (100 mL) and extracted into ethyl acetate (2×50 mL). The aqueous phase was evaporated to dryness to give the title compound as a white solid. δH (D2O): 0.52–0.63 (0.5H, m), 1.12–1.23 (0.5H, m), 1.26–1.38 (1H, m), 1.42–1.50 (0.5H, m), 1.59–1.69 (0.5H, m), 1.72–1.82 (1H, m), 2.61–2.71 (0.5H, m), 2.91–3.15 (4H, m), 3.33–3.47 (1H, m), 3.69–3.78 (1H, m), 3.88–3.96 (1H, m), 4.60–4.72 (1H, m), 7.02–7.11 (2H, m), 7.14–7.26 (2H, m).

1. customThe solvent was removed in vacuo
2. dissolutionthe residue was dissolved in water (100 mL)
3. extractionextracted into ethyl acetate (2×50 mL)
4. customThe aqueous phase was evaporated to dryness

ORD record

ord-ae13250f2e7b44b4b50e3af7bbf64cf3

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07405210B2