Triphenylphosphine → 1,1-Dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate

Participants

Reaction Steps

1,1-Dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.88 g, 83%) was prepared as a light yellow solid from 2-bromo-5-hydroxypyridine (0.50 g, 2.87 mmol), N-Boc-4-piperidinemethanol (0.64 g, 2.87 mmol) and Ph3P (0.77 g, 2.87 mmol) in THF (15 mL) followed by diisopropyl azodicarboxylate (0.62 g, 94%, 2.87 mmol) in THF (5 mL) in a manner similar to Example 1, Step 2. The material was purified by chromatography on a silica gel column eluted with 5 to 20% EtOAc/hexanes. 1H NMR (400 MHz, CDCl3): δ 8.04 (bs, 1H), 7.36 (d, 1H, J=8.8 Hz), 7.15-7.05 (m, 1H), 4.25-4.10 (m, 2H), 3.82 (d, 2H, J=6.1 Hz), 2.80-2.70 (m, 2H), 2.05-1.90 (m, 1H), 1.85-1.75 (m, 2H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 393/395 (M+Na).

Provenance & Evidence