1,4-Dioxane hydrochloride → (R)-1-(4-((3-(3-amino-1-hydroxypropyl)phenoxy)methyl)piperidin-1-yl)ethanone

Participants

Reaction Steps

HCl/dioxane (4M, 2 mL) was added to a solution of (R)-tert-butyl (3-(3-((1-acetylpiperidin-4-yl)methoxy)phenyl)-3-hydroxypropyl)carbamate (0.60 g, 1.40 mmol) in CH2Cl2 (10 mL) at 0° C. and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure to give after purification by triturating in diethyl ether Example 11 hydrochloride as a white solid. Yield (0.40 g, 88%); 1H NMR (400 MHz, DMSO-d6); δ 7.18 (t, J=7.8 Hz, 1H), 6.84 (d, J=7.6 Hz, 2H), 6.75 (d, J=7.6 Hz, 1H), 4.60 (t, J=6.4 Hz, 1H), 4.38 (d, J=14.8 Hz, 1H), 4.11 (s, 2H), 3.79 (d, J=6 Hz, 3H), 3.02 (t, J=11.2, 1H), 2.64 (d, J=3.2 Hz, 2H), 2.54 (s, 1H), 1.97 (s, 4H), 1.76 (t, J=16.0 Hz, 2H), 1.66-1.61 (m, 2H), 1.26-1.04 (m, 2H); MS: m/z 307.01 [M+H]+.

Provenance & Evidence