Trifluoroacetic acid → HCID 68108969, compound

Participants

Reaction Steps

To the product obtained in step B (40.0 mg, 0.12 mmol) was added triethylsilane (0.5 mL, 3.22 mmol), trifluoroacetic acid (0.35 mL, 4.51 mmol) and boron trifluoride-diethylether complex (0.65 mL, 4.51 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 24 h under a nitrogen atmosphere, quenched with 20% potassium carbonate solution (15 mL) and extracted with dichloromethane. The organic extract was washed with water followed by brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 dichloromethane/methanol). The product was converted to hydrochloride salt by dissolving in dichloromethane and treating with 2 M HCl in diethyl ether at 0° C. After stirring for 20 min the reaction mixture was concentrated in vacuo to give 6-chloro-8-(1-phenylethyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (32 mg, 90%, AUC HPLC 96.5%) as an off-white solid: mp 245-255° C. dec.; 1H NMR (CD3OD, 400 MHz) δ 7.38 (d, J=0.8 Hz, 1H), 7.31-7.20 (m, 5H), 7.20-7.14 (m, 1H), 4.39 (s, 2H), 4.27 (q, J=7.2 Hz, 1H), 3.67 (t, J=6.0 Hz, 2H), 3.18 (t, J=6.0 Hz, 2H), 1.67 (d, J=7.2 Hz, 3H); APCI MS m/z 312 [M+H]+

Provenance & Evidence