Tetrahydrofuran → HCID 22005217, compound

Participants

Reaction Steps

The intermediate obtained in Step A (359 mg, 0.961 mmol) was dissolved in 40 mL of dry THF, for a dropwise addition of a solution of LAH (1M/THF, 1.92 mL, 2 eq.). The reaction mixture was stirred at reflux for 24 hours then cooled to room temperature and quenched with water (80 μL), 20% NaOH (80 μL), and water (160 μL). After filtration, the solvent was evaporated to afford a residue which was filtered through to a pad of silica (10% ethyl acetate/hexane) to afford the title compound as a white solid (281 mg, 0.72 mmol, 85%). 1H NMR (300 MHz, CDCl3): δ 7.13 (m, 4 H), 4.32 (dq, J=5.2 J=11.4 Hz, 1 H), 4.11 (q, J=6.3 Hz, 1 H), 3.77 (septet, J=6.6 Hz, 1 H), 3.42 (septet, J=6.6 Hz, 1 H), 3.10 (s, 3 H), 1.29 (m, 16 H). FAB-MS: calcd for (C21H28FNO2) 345, found 346 (M+H). Anal. Calcd for C21H28NO2F: C, 76.84; H, 8.69; N, 3.90. Found: C, 76.67; H, 8.76; N, 3.77. mp 151-153° C. Rf=0.4 (20% ethyl acetate/hexane).

Provenance & Evidence