Hydrochloric Acid → HCID 25139337, compound

Participants

Reaction Steps

A solution of silyl ether 139 (488 mg, 1.07 mmol), and 1 M HCl (1.18 mL) in MeOH (30 mL) was stirred at 20° C. for 3 h. The solvent was evaporated and the residue was crystallised from MeOH/EtOAc to give alcohol 140 (357 mg, 88%) as the hydrochloride salt: mp (MeOH/EtOAc) 210-212° C.; 1H NMR [(CD3)2SO] δ 11.19 (s, 1H, HCl), 8.16 (s, 1H, H-9), 7.80 (s, 1H, H-5), 4.70 (br s, 1H, OH), 3.75-3.99 (m, 4H, 2×CH2O), 3.41 (d, J=6.6 Hz, 2H, CH2O), 3.33-3.51 (m, 2H, CH2N), 3.11-3.27 (m, 4H, CH2N, H-8), 2.87-3.11 (m, 6H, 2×CH2N, CH2), 2.59-2.71 (m, 1H, H-7), 2.22-2.32 (m, 2H, CH2); 13C NMR [(CD3)2SO] δ 163.6, 154.2, 148.4, 146.7, 131.8, 122.5, 113.8, 63.5, 63.0 (2), 55.0, 50.9 (2), 41.6, 35.4, 35.1, 33.1, 20.8. Anal. calcd for C18H24N4O3.HCl.¼CH3OH: C, 56.4; H, 6.7; N, 14.4. Found: C, 56.3; H, 6.4; N, 14.6%.

Provenance & Evidence