Morpholine → HCID 12000045, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 21 (6.05 g, 13.5 mmol, 1.0 equiv) in THF (135 mL) at room temperature, was added morpholine (11.8 mL, 135.6 mmol, 10 equiv), then tetrakis(triphenylphosphine)palladium(0) (1.56 g, 1.35 mmol, 0.1 equiv) in the dark. The solution was warmed to 47° C. The reaction was stirred at 47° C. for 10 hours, after which time the solution was cooled to room temperature and the THF was removed under reduced pressure. Purification by flash chromatography (30% EtOAc/hexane→100% EtOAc) afforded 22 (3.9 g, 90%) as a brown solid with a minor amount of Ph3PO. Rf=0.2 (EtOAc); FTIR (film, cm−1) 2938, 2866, 1515, 1462, 1251, 1105; 1H NMR (500 MHz, CDCl3) δ7.01 (d, J=8.5 Hz, 2H), 6.71 (d, J=8.5 Hz, 2H), 4.5 (br s, 2H), 3.75 (dd, J=10.0, 3.5 Hz, 1H), 3.61, (dd, J=9.5, 6.5 Hz, 1H), 3.19 (br s, 1H), 2.79 (dd, J=13.3, 6.0 Hz, 1H), 2.64 (dd, J=13.8, 7.5 Hz, 1H), 1.05 (m, 21H); 13C NMR (100 MHz, CDCl3) δ155.1, 130.3, 129.1, 115.8, 115.6, 66.2, 54.9, 37.9, 18.1, 11.9; HRMS (ES+) calculated for C18H33NO2Si (M+H)+: 324.2281, found: 324.2374.

Provenance & Evidence