Sodium Hydroxide → (R)-1-Methyl-5-(3-(4-(methylsulfonyl)phenyl)-3-o-tolylpropanoyl)pyridin-2(1H)-one

Participants

Reaction Steps

L-proline (44.9 mg, 390 μmol) was combined with dimethyl sulfoxide (5 mL), then sodium hydroxide (15.6 mg, 390 μmol) was added and the reaction stirred at room temperature for 30 min. Then (R)-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one (example 223, step 3; 200 mg, 487 μmol), sodium methanesulfinate (410 mg, 3.9 mmol) and copper(I) iodide (74.3 mg, 390 μmol) were added. The reaction mixture was heated at 120° C. for 21 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (SiO2; gradient ethyl acetate/heptane 1:1 to ethyl acetate) afforded the title compound (176 mg, 88%). White foam, MS (ESI+): m/z=: 410.2 [M+H]+.

Provenance & Evidence