Potassium Carbonate → HCID 59330542, compound

Participants

Reaction Steps

To a stirred solution of 5-bromo-3-(1-tert-butoxycarbonyl-2(S) -azetidinylmethoxy)pyridine (720 mg, 2.1 mmol), K2CO3 (725 mg, 5.25 mmol), PPh3 (50 mg) in DME (5 mL) and H2O (5 mL) was added 10% Pd/C (50 mg) and CuI (50 mg). The mixture was stirred at room temperature for 30 min under argon, then 5-hexyn-1-ol (0.8 mL) was added. The reaction mixture was refluxed for 72 h. After cooled, the mixture was filtered through Celite and washed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified by chromatography with hexane-EtOAc (1:2) and then EtOAc to give an oil (630 mg, 83%), [α]D−37.1 (c 1.9, CHCl3). 1H NMR (CDCl3) δ 8.22 (d, 2H, J=2.1 Hz), 7.24 (t, 1H, J=2.1 Hz), 4.50 (m, 1H), 4.32 (m, 1M), 4.11 (dd, 1H, J=10.2, 3.0 Hz), 3.88 (t, 2H, J=7.5 Hz), 3.75-3.65 (m, 2H), 2.47 (t, 2H, J=6.9 Hz), 2.41-2.20 (m, 2H), 1.95 (s, 1H), 1.80-1.64 (m, 4H), 1.42 (s, 9H); 13C NMR (CDCl3) δ 156.13, 154.40, 144.75, 137.13, 123.26, 121.18, 93.48, 79.76, 77.45, 68.68, 62.20, 60.00, 47.06, 31.82, 28.36, 24.80, 19.18, 19.01.

Provenance & Evidence