P-Chloroacetophenone → Methyl {1-[1-(4-chlorophenyl)ethyl]azetidin-3-ylidene}(3,5-difluorophenyl)acetate

A solution of 0.142 g (0.5 mmole) of methyl azetidin-3-ylidene(3,5-difluorophenyl)acetate, 0.142 g (1 mmol) of 4-chloroacetophenone and 0.15 mL (12 mmol) of triethylamine in 5 mL of dichloroethane was stirred at room temperature. After 5 min, 0.422 g (2 mmol) of sodium triacetoxyborohydride was added and the mixture was stirred at room temperature for 3 h. The reaction was quenched by addition of saturated KHCO3 solution and the mixture was partitioned between 10 mL ether and 2 mL saturated KHCO3 solution. The layers were separated and the organic layer was dried over Na2SO4, and concentrated. The residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm) using a gradient of CH3CN—H2O-Et3N (20:80:0.1 to 60:40:0.1) to afford the title compound; Mass Spectrum: m/e=378 (M+1 35Cl) and 380 (M+1 35Cl).

1. customThe reaction was quenched by addition of saturated KHCO3 solution
2. customthe mixture was partitioned between 10 mL ether and 2 mL saturated KHCO3 solution
3. customThe layers were separated
4. dry with materialthe organic layer was dried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm)

ORD record

ord-0de440b1db484c91a738633f6dce88c8

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906503B2