tert-butyl azetidin-3-ylmethyl(methyl)carbamate Chemical Properties

Boiling point:

267℃

Density 

1.012

Flash point:

116℃

storage temp. 

2-8°C(protect from light)

pka

10.86±0.40(Predicted)

Safety Information

HazardClass 

IRRITANT

tert-butyl azetidin-3-ylmethyl(methyl)carbamate Usage And Synthesis

Uses

Tert-butyl azetidin-3-ylmethyl(methyl)carbamate is an important organic reagent that can be used as a building block for the synthesis of tert-butyl ((1-((4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methyl)azetidin-3-yl)methyl)(methyl)carbamate which is an important intermediate of a selective small-molecule PLK inhibitors useful in the treatment of cell proliferative disorders.

Synthesis

A solution of tert-butyl ((1-benzhydrylazetidin-3-yl)methyl)carbamate (6.18 g, 17.53 mmol) in 50 mL of MeOH and 15 mL of EtOAc was purged with argon. Pd/C (10%, 50% in water) (929 mg) was added and the mixture was then purged again with argon and stirred in an H2 atmosphere for 18 h. The reaction was filtered through Ceitte and the filter was washed with EtOAc and MeOH, The resulting solvent was evaporated to dryness, providing 5.66 g of a mixture of tert-butyl azetidin-3-ylmethyl(methyl)carbamate together with one equivalent of diphenylmethane. The pure product tert-butyl azetidin-3-ylmethyl(methyl)carbamate was obtained after further purification.