Aluminium lithium hydride → HCID 22005208, compound

Participants

Reaction Steps

To the intermediate obtained in Step A (20 mg, 0.054 mmol) in dry THF (10 mL) was added dropwise LAH (2 eq., 1M, 0.11 mL) under argon and the mixture was stirred at reflux for 1 h. The reaction was quenched with water (3.9 μL), 20% NaOH (3.9 μL), and water (7.8 μL) again. Concentration afforded a white solid. The product was subjected to a pad of silica gel (CH2Cl2) to afford the title compound as a white solid (14 mg, 0.038mmol, 70%). 1H NMR (300 MHz, CDCl3): δ 7.39 (m, 2 H), 7.12 (m, 2 H), 3.52 (t, J=5.5 Hz, 2 H), 3.23 (m, 2 H), 2.60 (t, J=2.9 Hz, 2 H), 2.20 (t, J=3.7 Hz, 2 H), 1.30 (m, 14 H), 1.11 (m, 4 H), 0.771 (t, J=6.3 Hz, 3 H). FAB-MS: calcd for (C24H34FNO) 371, found 372 (M+H). Anal. Calcd for C24H34FNO: C, 77.59; H, 9.22; N, 3.77. Found: C, 77.57; H, 9.44; N, 3.05. mp 81-83° C. Rf=0.6 (10% ether/hexane).

Provenance & Evidence