Ammonium Chloride → tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

Participants

Reaction Steps

A solution of 1-Boc-azetidin-3-one (3.5 g, 20 mmol) in 50 mL and Et2O was cooled to 0° C. and 3M MeMgBr in Et2O (10 mL, 30 mmol) was added dropwise over 1 h. After 45 min, the reaction was allowed to warm to rt and stir an additional for 18 h. Then ½ sat'd NH4Cl (aq.) was added and the mixture extracted with EtOAc (2×). The combined organic layers were dried and the resulting semisolid was purified by RP HPLC (Agilent) to give the title compound as a white solid (3.2 g, 84%). 1H NMR (CDCl3): 3.84 (q, J=9.2 Hz, 4H), 1.97 (bs, 1H), 1.52 (s, 3H), 1.44 (m, 9H).

Provenance & Evidence