Benzyl chloroformate → Benzyl 3-hydroxyazetidine-1-carboxylate

Temperature

0 °C

To a solution of azetidin-3-ol hydrochloride (2 g, 18.26 mmol, 1.00 equiv) and sodium hydroxide (1.53 g, 38.25 mmol, 2.10 equiv) in water (10 mL) and tetrahydrofuran (25 mL) was added Cbz-Cl (3.27 g, 19.17 mmol, 1.05 equiv) dropwise with stirring at 0° C. over 30 min. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of 20 mL of water. The mixture was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×40 mL of sodium chloride (sat.). The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). Purification afforded 2.0 g (53%) of benzyl 3-hydroxyazetidine-1-carboxylate (50.2) as a light yellow liquid.

1. stirringThe resulting solution was stirred for 3 h at room temperature
2. customThe reaction was then quenched by the addition of 20 mL of water
3. extractionThe mixture was extracted with 3×30 mL of ethyl acetate
4. washThe resulting mixture was washed with 2×40 mL of sodium chloride (sat.)
5. dry with materialThe mixture was dried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customPurification

ORD record

ord-1778d591842d4a89bf321acfa641a7ef

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969557B2