Triphenylphosphine → tert-Butyl 4-{[(6-chloropyridin-3-yl)oxy]methyl}piperidine-1-carboxylate

Participants

Reaction Steps

1,1-Dimethylethyl 4-{[(6-chloro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (0.80 g, 54%) was prepared as a white solid from 2-chloro-5-hydroxypyridine (0.60 g, 4.51 mmol), N-Boc-4-piperidinemethanol (1.0 g, 4.51 mmol) and Ph3P (1.20 g, 4.51 mmol) in THF (25 mL) followed by diisopropyl azodicarboxylate (0.97 g, 94%, 4.51 mmol) in THF (8 mL) in a manner similar to Example 1, Step 2. 1H NMR (400 MHz, CDCl3): δ 8.04 (bs, 1H), 7.25-7.15 (m, 2H), 4.20-4.10 (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 327 (M+H).

Provenance & Evidence