Water → (R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of potassium 4-tert-butylcyclohexylmethyltrifluoroborate (100 mg, 0.0004 mol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (31.4 mg, 0.0000384 mol), (R)-6-(4-methyl-2-oxooxazolidin-4-yl)naphthalen-2-yl trifluoromethanesulfonate (144 mg, 0.000384 mol) and cesium carbonate (0.376 g, 0.00115 mol) in 1,4-dioxane (4.6 mL, 0.059 mol) and water (0.5 mL, 0.03 mol) was heated at reflux under a nitrogen atmosphere. The reaction mixture was stirred at 100° C. overnight, then cooled to room temperature, and diluted with EtOAc, filtrate, followed by extraction of ether. The organic layers were combined and dried over MgSO4, and filtered. The concentrated residue was chromatographed with silica gel under 0-100% EtOAc/hexane to give (R)-4-(6-((4-tert-butylcyclohexyl)methyl)naphthalen-2-yl)-4-methyloxazolidin-2-one as a solid (18.6 mg, 12.8%). 1H NMR (400 MHz, CHLOROFORM-d) δ=7.84 (d, J=8.7 Hz, 1 H), 7.79 (br. s., 1 H), 7.77 (d, J=8.5 Hz, 1 H), 7.60 (s, 1 H), 7.45 (dd, J=1.9, 8.6 Hz, 1 H), 7.38 (d, J=8.4 Hz, 1 H), 5.83 (br. s., 1 H), 4.46-4.39 (m, 2 H), 2.82 (d, J=7.9 Hz, 2 H), 2.09 (m., 1 H), 1.87 (s, 3 H), 1.68-1.40 (m, 5 H), 1.39-1.24 (m, 2 H), 1.08-0.96 (m, 1 H), 0.91 (s, 9 H).

Provenance & Evidence