Sodium hydride → HCID 68294434, compound

Temperature

0 °C

(2-Chloro-4-(methoxycarbonyl)benzyl)triphenylphosphonium bromide (1.04 g, 1.98 mmol) was dissolved in N,N-dimethylformamide (DMF, 20 mL) and the solution was cooled to 0° C. A 60% suspension of NaH in paraffin oil (80 mg, 2.00 mmol) was added and the reaction mixture was stirred at 0° C. for 15 mins. A solution of tert-butyl 3-oxoazetidine-1-carboxylate (0.32 g, 1.87 mmol) in anhydrous DMF (5 mL) was added and the reaction mixture was heated overnight at 65° C. After completion of the reaction as indicated by HPLC/MS, the cooled reaction mixture was diluted with EtOAC (20 mL) and quenched with a saturated NH4Cl solution (10 mL). The organic layer was washed with water (3×20 mL) and brine (15 mL). It was then dried over anhydrous Na2SO4, filtered and evaporated to get the crude product. This crude was purified by silica gel column chromatography using 50-80% EtOAc in Hexanes as eluent to provide tert-butyl 3-(2-chloro-4-(methoxycarbonyl)benzylidene)azetidine-1-carboxylate (0.27 g) as a white solid. ES+(M+Na)+360.

1. temperaturethe reaction mixture was heated overnight at 65° C
2. customAfter completion of the reaction
3. customthe cooled reaction mixture
4. additionwas diluted with EtOAC (20 mL)
5. customquenched with a saturated NH4Cl solution (10 mL)
6. washThe organic layer was washed with water (3×20 mL) and brine (15 mL)
7. dry with materialIt was then dried over anhydrous Na2SO4
8. filtrationfiltered
9. customevaporated
10. customto get the crude product
11. customThis crude was purified by silica gel column chromatography

ORD record

ord-64b9ca3ea5404fe08fff9a95aa8b8b02

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957066B2