Trifluoroacetic acid → Carbamate

Participants

Reaction Conditions

Reaction Steps

(E)-1-(2-Nitrovinyl)-2-(trifluoromethyl)benzene (230.8 mg, 1.063 mmol) and methyl-methoxymethyltrimethylsilanyl-methylamine (206 mg, 1.275 mmol) was dissolved in DCM (4 mL) and cooled to 0° C. under N2. Trifluoroacetic acid (8.19 μL, 0.106 mmol) was then added and the reaction mixture was stirred at 0° C. for 30 min then warmed to room temperature and stirred for 2 h. The reaction mixture was diluted with DCM and washed with brine. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo while loading onto silica gel. The residue was purified by flash chromatography (7-60% EtOAc-hexanes) to give (3S and R,4R and S)-1-methyl-3-nitro-4-(2-(trifluoromethyl)phenyl) pyrrolidine. 1H NMR (500 MHz, DMSO-d6) δ 7.84-7.65 (m, 3H), 7.5 (t, J=7.4 Hz, 1H), 5.40-5.34 (m, 1H), 4.18-4.10 (m, 1H), 3.40 (dd, J=3.0, 11.3 Hz, 1H), 3.20 (t, J=8.4 Hz, 1H), 3.10-3.04 (m, 1H), 2.40-2.28 (m, 1H), 2.3 (s, 3H).

Provenance & Evidence