Trifluoroacetic acid → HCID 68108521, compound

Participants

Reaction Steps

To a solution of the product of step A (50.0 mg, 0.12 mmol) in dichloromethane (4 mL) was added trifluoroacetic acid (0.4 mL). After stirring for 2 h at ambient temperature the reaction mixture was quenched with 10% sodium bicarbonate solution (15 mL) and extracted with dichloromethane. The organic extract was 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-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-8-yl)(phenyl)methanol hydrochloride (18 mg, 47%, AUC HPLC 97.1%) as a white solid: mp 260° C. dec.; 1H NMR (CD3OD, 300 MHz) δ 7.46 (s, 1H), 7.41-7.20 (m, 6H), 5.85 (br s, 1H), 4.40 (s, 2H), 3.68 (t, J=6 Hz, 2H), 3.25-3.15 (m, 2H); APCI MS m/z 314 [M+H]+.

Provenance & Evidence