1-Acetyl-3-hydroxyazetidine Chemical Properties

Boiling point:

275.9±33.0 °C(Predicted)

Density 

1.275±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

13.31±0.20(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HS Code 

2933998090

1-Acetyl-3-hydroxyazetidine Usage And Synthesis

Synthesis

Step 1 - Synthesis of 1-(3-hydroxyazetidin-1-yl)ethan-1-one: Azetidin-3-ol (3.0 g, 27.40 mmol) and triethylamine (8.33 g, 82.48 mmol) were dissolved in tetrahydrofuran (150 mL) and stirred for 10 min at -78°C. Slowly, acetyl chloride (2.15 g, 27.39 mmol) was added dropwise. Acetyl chloride (2.15 g, 27.39 mmol) was added slowly dropwise, keeping the reaction temperature at -78°C. After completion of the dropwise addition, the reaction mixture was warmed up to 20-30°C and stirring was continued for 3 hours. After completion of the reaction, the insoluble solids were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent methanol/ethyl acetate (1/10, v/v) to afford 500 mg (14% yield) of 1-(3-hydroxyazetidin-1-yl)ethan-1-one as a yellow oil. The product was characterized by 1H NMR (400 MHz, DMSO): δ 3.60 (t, J = 4.8 Hz, 2H), 2.83 (t, J = 4.8 Hz, 2H), 2.21 (s, 3H).

References

[1] Patent: US2012/214762, 2012, A1. Location in patent: Page/Page column 169
[2] Patent: US5130309, 1992, A