Triphenylphosphine → 3-[(4'-Nitro-1,1'-biphenyl-4-yl)oxy]quinuclidine

Participants

Reaction Steps

3-Quinuclidinol (Aldrich, 0.51 g, 4 mmol) coupled with 4′-nitro-1,1′-biphenyl-4-ol (TCl, 0.43 g, 2 mmol) with DIAD (di-isopropyl azadicarboxylate, Aldrich, 0.81 g, 4 mmol) and Ph3P (Aldrich, 1.04 g, 4 mmol) in THF (anhydrous, Aldrich, 40 mL) at ambient temperature for two days. The reaction mixture was concentrated. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as solid (400 mg, yield, 62%). 1H NMR (300 MHz, CD3OD) δ 1.45–1.57 (m, 1H), 1.63–1.91 (m, 2H), 1.97–2.12 (m, 1H), 2.17–2.24 (m, 1H), 2.66–3.00 (m, 5H), 3.30–3.41 (m, 1H), 4.56–4.64 (m, 1H), 7.05 (dt, J=8.8, 2.6 Hz, 2H), 7.68 (dt, J=9.2, 2.6 Hz, 2H), 7.82 (dt, J=8.8, 2.7 Hz, 2H), 8.28 (dt, J=8.8, 2.8 Hz, 2H) ppm. MS (DCl/NH3) m/z 325 (M+H)+.

Provenance & Evidence