Triphenylphosphine → 1,1-Dimethylethyl 4-({[4-(5-bromo-2-pyridinyl)phenyl]oxy}methyl)-1-piperidinecarboxylate

Participants

Reaction Steps

1,1-Dimethylethyl 4-({[4-(5-bromo-2-pyridinyl)phenyl]oxy}methyl)-1-piperidinecarboxylate (0.27 g, 60%) was prepared as a white solid from 4-(5-bromo-2-pyridinyl)phenol (0.25 g, 1.0 mmol), N-Boc-4-piperidinemethanol (0.23 g, 1.0 mmol) and Ph3P (0.27 g, 1.0 mmol) in THF (7 mL) followed by diisopropyl azodicarboxylate (0.22 g, 94%, 1.0 mmol) in THF (3 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 8.69 (s, 1H), 7.92 (d, 2H, J=8.8 Hz), 7.85 (d, 1H, J=8.5 Hz), 7.57 (d, 1H, J=8.5 Hz), 6.97 (d, 2H, J=8.8 Hz), 4.25-4.10 (m, 2H), 3.86 (d, 2H, J=6.4 Hz), 2.85-2.70 (m, 2H), 2.05-1.90 (m, 1H), 1.90-1.80 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 446/448 (M+H).

Provenance & Evidence