Pyridine → HCID 86667166, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4 (416 mg, 2.09 mmol) and pyridine (506 μL, 6.27 mmol) in CH2Cl2 (10 mL), Tf2O (421 μL, 2.51 mmol) was dropwise added at −10° C. The mixture was left to react for 10 min when it was diluted (CH2Cl2), washed (HCl(aq) 5%, NaHCO3(aq) sat, brine), dried (MgSO4), filtered and concentrated. The crude was then dissolved in DMF (20 mL). Bu4NNO2 (1810 mg, 6.27 mmol) was added and the mixture was heated to 50° C. After 1 h the mixture was cooled to room temperature. and concentrated. Purification was made by flash chromatography using EtOAc:n-heptan (1:1) as eluent. The reaction yielded 64% of 8. 1H-NMR (CDCl3) 4.79 (dd, J=4.78, 9.75 Hz, 1 H), 4.17 (m, 1 H), 3.83 (ddd, J=4.58, 9.84, 11.29 Hz, 1 H), 2.18 (s, 3 H), 2.00-2.10 (m, 1 H), 1.85-1.95 (m, 1 H), 1.70-1.80 (m, 1 H), 1.50-1.65 (m, 2 H), 1.30-1.45 (m, 1 H)

Provenance & Evidence