Potassium Carbonate → HCID 67429189, compound

Participants

Reaction Steps

To a stirred solution of 5-bromo-3-(1-tert-butoxycarbonyl-2(S)-pyrrolidinylmethoxy)pyridine (800 mg, 2.24 mmol), K2CO3 (745 mg, 5.40 mmol), PPh3 (55 mg) in DME (4 mL) and H2O (4 mL) was added 10% Pd/C (55 mg) and CuI (55 mg). The mixture was stirred at room temperature for 30 ml under argon, then 5-hexyn-1-ol (1.0 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 (1:1) to give an oil (800 mg, 95%), [α]D=−35.5 (c 2.2, CHCl3). 1H NMR (CDCl3) δ 8.19 (m, 2H), 7.23 (m, 1H), 4.14 (m, 2H), 4.05-3.75 (m, 1H), 3.75-3.69 (m, 2H), 3.50-3.25 (m, 2H), 2.47 (t, 2H, J=6.6 Hz), 2.10-1.64 (m, 9H), 1.47 (s, 9H); 13C NMR (CDCl3) δ154.70, 154.36, 144.76 and 144.49, 137.29 and 137.00, 123.04, 121.15, 93.32, 79.96 and 79.56, 68.69 and 68.33, 62.28, 55.94 and 55.64, 46.97 46.59, 31.82, 28.51, 28.00, 24.79, 23.84, 22.83, 19.20.

Provenance & Evidence