Triphenylphosphine → 4-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Participants

Reaction Steps

1-Methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.71 g, 58%) was prepared as a light yellow solid from 2-bromo-5-hydroxypyridine (0.60 g, 3.45 mmol), 1-methylethyl 4-(hydroxymethyl)-1-piperidinecarboxylate (prepared as in Example 9, Step 1, 0.71 g, 3.45 mmol) and Ph3P (0.92 g, 3.45 mmol) in THF (18 mL) followed by diisopropyl azodicarboxylate (0.75 g, 94%, 3.45 mmol) in THF (6 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 8.04 (bs, 1H), 7.36 (d, 1H, J=8.8 Hz), 7.15-7.05 (m, 1H), 4.91 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.82 (d, 2H, J=6.1 Hz), 2.85-2.70 (m, 2H), 2.05-1.90 (m, 1H), 1.90-1.75 (m, 2H), 1.35-1.15 (m, 8H); LRMS (ESI), m/z 357/359 (M+H).

Provenance & Evidence