Methanol → Methyl azetidine-3-carboxylate hydrochloride

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).

1. customThe resulting clear, light yellow solution was sealed
2. concentrationIn the morning the reaction mixture was concentrated in vacuo
3. additionthe resulting oil was treated with 100 mL anhydrous benzene
4. concentrationconcentrated in vacuo
5. customto give a solid
6. customThe resulting light yellow solid was dried in vacuo

ORD record

ord-9c0bff5c367c4f6897fee162b254c8e2

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842685B2