Hydrochloric Acid → HCID 25139186, compound

Participants

Reaction Steps

A solution of silylether 135 (1.57 g, 4.37 mmol), and 1 N HCl (5 mL) in MeOH (40 mL) was stirred at 20° C. for 1 h. The solution was partitioned between EtOAc and water. The organic layer was dried, the solvent evaporated and the residue was purified by chromatography, eluting with a gradient (0-2%) of MeOH/DCM, to give alcohol 142 (0.84 g, 79%) as a yellow solid: mp (MeOH/EtOAc) 122-123° C.; 1H NMR [(CD3)2SO] δ 8.13 (s, 1H, H-9), 7.77 (s, 1H, H-5), 4.71 (t, J=5.2 Hz, 1H, OH), 3.42 (dd, J=6.4 Hz, 5.2 Hz, 2H, CH2O), 3.11-3.20 (m, 2H, CH2), 2.86-2.96 (m, 4H, CH2), 2.59-2.71 (m, 1H, H-7), 1.32 (t, J=7.5 Hz, 3H, CH3); 13C NMR [(CD3)2SO] δ 165.9, 153.9, 148.1, 146.8, 131.6, 122.5, 113.8, 63.5, 41.6, 35.3, 35.0, 29.6, 11.8. Anal. calcd for C13H15N3O2: C, 63.7; H, 6.2; N, 17.1. Found: C, 63.9; H, 6.2; N, 17.4%.

Provenance & Evidence