4-Bromophenol → 4-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

Participants

Reaction Steps

4-{[(4-Bromophenyl)oxy]methyl}-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine (322 mg, 42%) was prepared from {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methanol (prepared as in Example 20, Step 3, 450 mg, 2.0 mmol), 4-bromophenol (346 mg, 2.0 mmol) and Ph3P (629 mg, 2.4 mmol) in THF (5 mL) followed by diisopropyl azodicarboxylate (0.512 mL, 2.6 mmol) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 2H, J=9.1 Hz), 6.76 (d, 2H, J=8.9 Hz), 4.28-4.18 (m, 2H), 3.79 (d, 2H, J=6.2 Hz), 3.14-3.04 (m, 2H), 2.94-2.82 (m, 1H), 2.10-1.94 (m, 1H), 1.97-1.87 (m, 2H), 1.49-1.36 (m, 2H), 1.28 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 380/382 (M+H).

Provenance & Evidence