1,4-Dioxane hydrochloride → HCID 86271762, compound

Participants

Reaction Steps

HCl/dioxane (4M, 2.5 mL) was added at 0° C. to a solution of tert-butyl ((3R)-3-hydroxy-3-(3-((tetrahydrofuran-2-yl)methoxy)phenyl)propyl)carbamate (0.25 g, 0.71 mmol) in DCM (10 mL) and the reaction mixture was stirred at room temperature for 2 h. After completion of the reaction the solvent was removed under reduced pressure. Purification by column chromatography (MeOH:DCM with 1% aq. NH4OH, 1-10% gradient) gave Example 14 as a mixture of diastereomers as an off white semi-solid. Yield (0.22 g, 95%); 1H NMR (400 MHz, DMSO-d6): δ 7.20 (t, J=8.0 Hz, 1H), 6.87 (d, J=8.0 Hz, 2H), 6.78-6.76 (m, 1H), 4.64-4.61 (m, 1H), 4.15-4.11 (dd, 1H), 3.93-3.87 (m, 2H), 3.78-3.75 (m, 1H), 3.70-3.64 (m, 1H), 2.69-2.66 (m, 2H), 2.01-1.95 (m, 1H), 1.88-1.79 (m, 2H), 1.70-1.65 (dd, J=6.8 Hz, 3H); MS: m/z 252.14 [M+H]+.

Provenance & Evidence