Aluminium lithium hydride → HCID 10403856, compound

Participants

Reaction Steps

The product from Example 15C in THF solution (30 mL) was treated with LAH (5.50 mmol) and stirred at room temperature for 2 hours. The mixture was treated with Na2SO4 decahydrate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (10% MeOH/CH2Cl2) to provide the title compound. The maleate salt was formed and recrystallization from ethanol/diethyl ether. 1H NMR (CD3OD, 300 MHz) δ 2.22-2.36 (m, 2H), 3.45-3.62 (m, 2H), 3.70 (s, 2H), 4.45-4.58 (m, 3H), 4.95 (s, 1H), 6.23 (s, 1H), 6.62-6.65 (m, 1H), 6.70 (t, J=3.0 Hz, 1H), 6.95 (dt, J=2.0, 6.0 Hz, 1H), 7.22 (dd, J=2.0, 8.0 Hz, 1H), 7.40-7.45 (m, 1H), 7.60 (t, J=2.0 Hz, 1H), 8.05 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 322 (M+H)+. Mp 211-214° C. Anal. Calcd for C19H19N4F.1.3 C4H4O4: C, 61.82;H, 5.36; N, 11.38. Found: C, 61.88;H, 4.99; N, 11.28.

Provenance & Evidence