Aluminium lithium hydride → HCID 22005325, compound

Participants

Reaction Steps

The intermediate obtained in Step A (375 mg, 0.905 mmol) was dissolved in dry THF (50 mL), treated dropwise with lithium aluminum hydride (1M/THF, 1.81 mL) and the reaction stirred at reflux for 24 hours. The reaction was quenched by the successive dropwise addition of water (0.1 ml), NaOH 20% (0.1 ml), and water again (0.3 ml). Concentration in vacuo afforded a white residue which was partitioned between CH2Cl2 and water. The organic layer was dried with MgSO4, filtered, and concentrated to afford an oil. The product was passed through a pad of silica (40% diethyl ether/hexanes) yielding an oil which slowly solidified to give the title compound as a white solid (295 mg, 0.76 mmol, 84%). 1H NMR (300 MHz, CDCl3): δ 7.14 (m, 4 H), 4.35 (d, 2 H), 3.53 (t, J=4.8 Hz, 4 H), 3.45 (m, 2 H), 3.18 (s, 2 H), 2.18 (t, J=4.5 Hz, 4 H), 1.26 (m, 13 H); FAB-MS calcd for (C23H31N2FO2) 386, found 387 (M+H). Anal. Calcd for C23H31N2O2F: C, 71.47; H, 8.08; N, 7.25; F, 4.92 Found: C, 71.55; H, 8.16; N, 7.05; F, 4.70. mp 93.5-95.5° C. Rf=0.4 (40% diethyl ether/hexane).

Provenance & Evidence