Triphenylphosphine → 1-Boc-4-(3-nitro-5-trifluoromethyl-phenoxy)-piperidine

Participants

Reaction Steps

A solution of 3-nitro-5-(trifluoromethyl)phenol (0.583 g, 2.82 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (0.850 g, 4.22 mmol), PPh3 (1.11 g, 4.22 mmol), DIAD (0.67 mL, 4.22 rnmol), and benzene (8.7 mL) was allowed to stir at rt until reaction was judged to be complete. The reaction mixture was concentrated. The resulting off-white solid was purified by column chromatography to give tert-butyl 4-(3-nitro-5-(trifluoromethyl) -phenoxy)piperidine-1-carboxylate (0.750 g, 66%). 1H NMR (400 MHz, CD3OD) δ: 8.05-7.97 (m, 2H), 7.64 (s, 1H), 4.84-4.78 (m, 1H), 3.75-3.69 (m, 2H), 3.42-3.35 (m, 2H), 2.03-1.96 (m, 2H), 1.77-1.69 (m, 2H), and 1.46 (s, 9H).

Provenance & Evidence