Methanol → Methyl azetidine-3-carboxylate hydrochloride

Participants

Reaction Steps

To a slurry of azetidine-3-carboxylic acid (20 g, 198 mmol) in 500 mL anhyd. MeOH under nitrogen at 0° C. was added slowly dropwise thionyl chloride (36 mL, 495 mmol) over 4 h. The resulting clear, light yellow solution was sealed and placed in a 0° C. freezer overnight. In the morning the reaction mixture was concentrated in vacuo, and the resulting oil was treated with 100 mL anhydrous benzene and concentrated in vacuo to give a solid. This was repeated anhydrous benzene. The resulting light yellow solid was dried in vacuo to give methyl azetidine-3-carboxylate hydrochloride. 1H NMR (400 MHz, MeOH-d4) δ ppm 4.21-4.30 (m, 4H), 3.78 (s, 3H), 3.71-3.78 (m, 1H).

Provenance & Evidence