Phenylsilane → 6-(2-Hydroxy-2-methylpropyl)-3-(1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-phenyl-1,3-oxazinan-2-one

Participants

Reaction Steps

To a solution of 3-(1-(4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl)cyclopropyl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (22 mg, 0.048 mmol) in 2:1 2-Propanol/CH2Cl2 (1.5 mL) was added cobalt catalyst A (catalytic amount, c.a. 1 mg), followed by addition of phenylsilane (100 μL, excess). The mixture was stirred vigorously in open air for 1 h. LC-MS found the reaction was complete. The mixture was quenched with 3% aq HCl, filtered, and purified by prep HPLC to afford the title compound (6.8 mg, 30%). LC-MS Method 1 tR=1.37 min., m/z 473 (M+1); 1H NMR (CD3OD) δ 7.69(d, 1H), 7.54(d, 2H), 7.42-7.39(m, 5H), 7.13(d, 2H), 6.74(s, 1H), 6.69(d, 1H), 3.59(s, 3H), 3.25(m, 1H), 2.89(m, 1H), 2.67-2.50(m, 2H), 2.19(s, 2H), 1.36-1.20(m, 3H), 1.25(s, 3H), 1.09(m, 1H), 0.95(s, 3H).

Provenance & Evidence