Triphenylphosphine → HCID 24994032, compound

Participants

Reaction Steps

The title compound was prepared as a white solid from 2-fluoro-4′-(methylsulfonyl)-4-biphenylol (0.25 g, 0.94 mmol), N-Boc-4-piperidinemethanol (0.21 g, 0.94 mmol) and Ph3P (0.25 g, 0.94 mmol) in THF (6 mL) followed by diisopropyl azodicarboxylate (0.20 g, 94%, 0.94 mmol) in THF (2 mL) in a manner similar to Example 1, Step 2. The crude product was triturated with hot hexane containing 1% of MeOH to give 20 mg of the title compound as a white solid. The filtrate was purified by chromatography on a silica gel column eluted with 3:4 EtOAc/hexane to give additional 0.34 g (overall 83%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.99 (d, 2H, J=8.3 Hz), 7.76 (d, 2H, J=7.4 Hz), 7.50-7.40 (m, 1H), 6.90-6.80 (m, 2H), 4.20-4.10 (m, 2H), 3.91 (d, 2H, J=6.4 Hz), 3.14 (s, 3H), 2.90-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.45 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 486 (M+Na).

Provenance & Evidence