Dimethylacetamide → 1-(6-Nitro-pyridin-3-yl)-azetidin-3-ol

Temperature

120 °C

A 50 mL round bottom flask with a magnetic stirrer and reflux condenser was charged with 3-hydroxyazetidine. HCl (2 g, 18.4 mmol), 5-bromo-2-nitropyridine (2.1 g, 10.2 mmol), diisopropylethylamine (5.4 mL, 30.7 mmol), tetrabutylammonium iodide (5.7 g, 15.4 mmol) and N,N-dimethylacetamide (10 mL). The mixture stirred at 120° C. for 16 h. After this time the mixture was cooled and ethyl acetate (25 mL) and water (25 mL) were added. The separated aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organics were washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with a gradient of 4:1 hexanes:ethyl acetate c-100 ethyl acetate to afford a 52% yield (1.9 g) of 128a.

1. temperatureA 50 mL round bottom flask with a magnetic stirrer and reflux condenser
2. temperatureAfter this time the mixture was cooled
3. extractionThe separated aqueous layer was extracted with ethyl acetate (2×10 mL)
4. washThe combined organics were washed with brine (20 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by column chromatography
9. washeluting with a gradient of 4:1 hexanes

ORD record

ord-54cd8214e57346b8a167bfacbdb9223d

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618107B2