Trifluoroacetic acid → HCID 53403834, compound

Temperature

40 °C

To a solution of N-methoxy-N-methyl-3-oxocyclopentanecarboxamide (2.43 g, 14.19 mmol) in 30 mL toluene under nitrogen was added deoxo-fluor® (7.05 mL, 38.3 mmol) followed by trifluoroacetic acid (0.219 mL, 2.84 mmol). The reaction was sealed and heated to 40° C. overnight. The reaction mixture was cooled, diluted with Et2O, cooled to 0° C. in an ice bath and quenched slowly with 75 mL 2N NaOH with rapid stirring. The aq. Layer was separated and extracted once with Et2O. The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purified by silica gel chromatography (50% EA/hexanes) gave (rac)-3,3-difluoro-N-methoxy-N-methylcyclopentanecarboxamide as a light yellow oil. 1H NMR (400 MHz, CDCl3-d) δ ppm 3.71 (s, 3 H), 3.29-3.43 (m, 1 H), 3.21 (s, 3 H), 2.17-2.54 (m, 3 H), 1.93-2.15 (m, 3 H).

1. customThe reaction was sealed
2. temperatureThe reaction mixture was cooled
3. temperaturecooled to 0° C. in an ice bath
4. customquenched slowly with 75 mL 2N NaOH with rapid stirring
5. customThe aq. Layer was separated
6. extractionextracted once with Et2O
7. washThe combined organics were washed with brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurified by silica gel chromatography (50% EA/hexanes)

ORD record

ord-69e56293184d4826a582be609c084acf

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842685B2