Trifluoroacetic acid → HCID 53403834, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence