1,4-Dioxane hydrochloride → HCID 86271855, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl 2-((3-((R)-3-((tert-butoxycarbonyl)amino)-1-hydroxypropyl)phenoxy)methyl)pyrrolidine-1-carboxylate (0.3 g, 0.66 mmol) in DCM (10 mL) was added HCl/dioxane (3 mL) at 0° C. and the reaction mixture was stirred at rt for 2 h. After completion of the reaction the solvent was removed in vacuo. The residue was purified by prep HPLC to give (R)-3-Amino-1-(3-((S)-pyrrolidin-2-ylmethoxy)phenyl)propan-1-ol (Example 22) as a white solid. Yield (0.18 g, 89%); 1H NMR (400 MHz, CD3OD) δ 7.31 (t, J=8.0 Hz, 1H), 7.07 (s, 1H), 7.03 (d, J=7.6 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 4.83-4.82 (m, 1H), 4.35 (dd, J=10.4, 3.2 Hz, 1H), 4.17-4.12 (m, 1H), 4.05-4.03 (m, 1H), 3.39-3.36 (m, 2H), 3.14-3.01 (m, 2H), 2.32-2.18 (m, 1H), 2.16-2.08 (m, 2H), 2.06-1.87 (m, 3H). MS: m/z 251.28 [M+H]+.

Provenance & Evidence