Methanol → Methyl azetidine-3-carboxylate hydrochloride

Temperature

5 °C

A stirred suspension of azetidine-3-carboxylic acid (2 g, 19.8 mmol) in MeOH (8 ml) was cooled to 5° C. in an ice-water bath. Thionyl chloride (4.3 ml, 59 mmol) was added dropwise at such a rate as to maintain reaction temperature below 30° C. A further portion of MeOH (8 ml) was added carefully and the mixture heated at 65° C. overnight. Evaporation of the solvent and co-evaporation with MeOH (2×20 ml) at reduced pressure provided the title compound as viscous brown oil that crystallized on standing (3.17 g, 100%). The material was used without purification.

1. temperatureto maintain
2. customreaction temperature below 30° C
3. temperaturethe mixture heated at 65° C. overnight
4. customEvaporation of the solvent and co-evaporation with MeOH (2×20 ml) at reduced pressure

ORD record

ord-672fa4ad5fc645698aab9596ee40bd19

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691804B2