Lithium Hydroxide → HCID 66666008, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-3-(4-bromophenyl)-1-(2-methylpyridin-4-yl)-3-o-tolylpropan-1-one (example 142, step 2; 2.00 g, 5.07 mmol), ethyl piperidine-4-carboxylate (1.2 g, 7.61 mmol), sodium tert-butoxide (975 mg, 10.1 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-biphenyl (484 mg, 1.01 mmol) and tris(dibenzylideneacetone)dipalladium(0) (464 mg, 507 μmol) in toluene (100 mL) was heated at 85° C. for 4 h and at room temperature for 17 h, then filtered through diatomaceous earth. After evaporation of volatile material, the residue was dissolved in tetrahydrofuran (50 mL), 1 M aq. lithium hydroxide solution (50 mL, 50 mmol) and methanol (15 mL), then after 2 h treated with 1 M aq. potassium hydrogensulfate solution (40 mL) and sat. aq. ammonium chloride solution (50 mL). The mixture was extracted with ethyl acetate, the organic layer washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography (SiO2; dichloromethane-methanol gradient) produced the title compound (2.24 g, 66%). Light yellow solid, MS (ESI−): m/z=441.3 ([M−H]−).

Provenance & Evidence