Sodium Bicarbonate → HCID 68109125, compound

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Reaction Steps

The product of step F (22 mg, 0.05 mmol) in 2N HCl diethyl ether solution (5 mL) was stirred at 0-5° C. for 2 h and then at ambient temperature for 4 h. After concentration in vacuo, the solid obtained was treated with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude material which was purified by flash column chromatography (SiO2, 80:18:2 dichloromethane/methanol/ammonium hydroxide) followed by semi-preparative HPLC. After concentration in vacuo, the solid obtained was treated with 1.25M HCl methanol solution (0.5 mL) and lyophilized to yield 9-(phenylsulfonyl)-2,3,4,5-tetrahydro-1H-benzofuro[3,2-c]azepine hydrochloride (2.8 mg, 15%, AUC HPLC 98.8%) as a white solid: mp 211-216° C.; 1H NMR (CD3OD, 300 MHz) δ 8.12 (s, 1H), 7.96 (dt, J=6.6, 1.8 Hz, 2H), 7.81 (dd, J=8.7, 1.8 Hz, 1H), 7.76-7.51 (m, 4H), 4.02 (s, 2H), 3.19 (br s, 2H), 3.05 (t, J=6.0 Hz, 2H), 1.95 (br s, 2H); ESI MS m/z 328 [M+H]+.

Provenance & Evidence