Imidazole → Benzyl 3-[tert-butyl(dimethyl)silyl]oxyazetidine-1-carboxylate

Into a 50-mL round-bottom flask was placed benzyl 3-hydroxyazetidine-1-carboxylate (2.15 g, 10.38 mmol, 1.00 equiv), TBSCl (2.34 g, 15.60 mmol, 1.50 equiv), imidazole (1.27 g, 18.68 mmol, 1.80 equiv) and N,N-dimethylformamide (15 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 30 mL of water. The mixture was extracted with 3×40 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×50 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 (1:5). Purification afforded 3.0 g (90%) of benzyl 3-[(tert-butyldimethylsilyl)oxy]azetidine-1-carboxylate (50.3) as a light yellow liquid.

1. customInto a 50-mL round-bottom flask was placed
2. customThe reaction was then quenched by the addition of 30 mL of water
3. extractionThe mixture was extracted with 3×40 mL of ethyl acetate
4. washThe resulting mixture was washed with 2×50 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-1adc90772226492e81b700fdbc889f58

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969557B2