Hydrochloric Acid → (2-Azetidin-2-yl-5-chlorophenyl)methanol hydrochloride

Participants

Reaction Conditions

Reaction Steps

LAH (1 M solution in ether, 7.74 mL) was added to a stirred solution of 4-(4-chloro-2-{[(triisopropylsilyl)oxy]methyl}phenyl)azetidin-2-one (0.7122 g, 1.935 mmol) in ether (2 mL) at 0° C. The solution was heated to reflux and after 2 h was cooled to 0° C. and quenched with water (0.294 mL), 15% sodium hydroxide solution (0.294 mL) and water (0.881 mL). The mixture was sonicated to give a uniform precipitate, filtered and evaporated in vacuo to an oil. The oil was dissolved in ethanol (10 mL) and concentrated HCl (0.167 mL, 2 mmol) was added with stirring at 0° C. The reaction was warmed to ambient temperature and after 30 min was evaporated in vacuo, azeotroping with ethanol to give (2-azetidin-2-yl-5-chlorophenyl)methanol hydrochloride (0.453 g) as a crystalline solid: 1H NMR (CD3OD, 400 MHz) δ 2.79 (m, 1H), 3.14 (m, 1H), 3.87 (dt, J=4.5 and 10.0 Hz, 1H, 4.18 (q, J=9.3 Hz, 1H), 4.61 (d, J=13.1 Hz, 1H), 4.68 (d, J=13.1 Hz, 1H), 5.93 (t, J=9.0 Hz, 1H), 7.49 (m, 2H), 7.69 (d, J=8.2 Hz, 1H).

Provenance & Evidence