Dimethylamine, hydrochloride → Tert-butyl 3-(dimethylcarbamoyl)azetidine-1-carboxylate

To 300 mg (1.49 mmol) azetidine-1,3-dicarboxylic acid mono-tert-butyl ester and 241.6 mg (1.79 mmol) 1-hydroxybenzotriazole hydrate in 20 mL DMF at 0° C., was added 364.5 mg (4.47 mmol) dimethylamine hydrochloride, and the reaction was stirred for 30 minutes. 342.8 mg (1.79 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, followed by 1.5 mL (8.94 mmol) DIPEA were added, and the reaction was stirred at room temperature for 3 hours. After evaporation of the solvent, the crude was diluted with 100 mL DCM. The organic phase was washed with a 2 M solution of HCl (2×50 mL), a saturated solution of NaHCO3 (2×50 mL), brine (2×50 mL), and dried over Na2SO4. After filtration, the solvent was evaporated to give the desired product which was used for the next step without further purification.

1. additionwere added
2. stirringthe reaction was stirred at room temperature for 3 hours
3. customAfter evaporation of the solvent
4. additionthe crude was diluted with 100 mL DCM
5. washThe organic phase was washed with a 2 M solution of HCl (2×50 mL)
6. dry with materiala saturated solution of NaHCO3 (2×50 mL), brine (2×50 mL), and dried over Na2SO4
7. filtrationAfter filtration
8. customthe solvent was evaporated

ORD record

ord-b52280c6418545c88b1c265275ddfa31

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346816B2