Reaction Steps
To a solution of (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)(6-(4-(4-fluorophenoxyl)phenyl)pyridin-2-yl)methanone (0.621, g, 1.58, mmol) in an 85:15, mixture of DCM/MeOH (10, mL) was added 4M HCl in dioxane (2, mL, 8, mmol). After stirring overnight 0.5, mL, water was added to the reaction. After 3, more hours the reaction was diluted with 50, mL DCM and solid NaHCO3, was added. After the bubbling subsided, the reaction mixture was dried over Na2SO4, filtered, and evaporated in vacuo to a residue. The residue was chromatographed over silica gel with 10-75% acetone in hexanes. The product fractions were isolated and evaporated in vacuo. The residue was dissolved in acetone, evaporated in vacuo, dissolved in EtOAc and hexanes, evaporated in vacuo, treated with hexanes, and evaporated in vacuo. The material was dried under vacuum at 50° C. to give the product (R)-1-(6-(4-(4-fluorophenoxy)phenyl)pyridin-2-yl)-2,3-dihydroxypropan-1-one as a glassy orange solid (0.155, g, 0.44, mmol, 28% yield). LC/MS: m/z=354.1, [M+H]+, ; 1H NMR (400, MHz, DMSO-d6): 8.23-8.17, (3 H, m), 8.08, (1 H, t, J=7.9, Hz), 7.88, (1 H, dd, J=7.7, Hz, 0.9, Hz), 7.32-7.25, (2 H, m), 7.20-7.15, (2 H, m), 7.12, (2 H, d, J=9.0, Hz), 5.54-5.49, (1 H, m), 5.09, (1 H, d, J=7.0, Hz), 4.78, (1 H, t, J=5.5, Hz), 3.93-3.81, (2 H, m). Unless otherwise indicated all 1H NMR chemical shifts reported herein are denoted by the delta (δ) scale.
