Dichloromethane → (S)-methyl 3-((2-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To (S)-benzyl 5-(chloromethyl)-2,3-dihydro-1H-inden-2-ylcarbamate (7.09 mmol, 2.24 g) in THF (44.9 mL) was added methyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(trifluoromethyl)benzoate (7.09 mmol, 2.242 g), Bromo(N-succinimidyl)bis-(triphenylphosphine)palladium(II) (0.355 mmol, 0.287 g) and sodium carbonate (45.0 mmol, 22.5 mL). The reaction was heated to 80° C. for 4 hrs. DCM was added before washing with water (×1) followed by brine (×1). The organics were dried over MgSO4 before removing the solvent in vacuo. The crude material was purified by silica chromatography (5:1>2:1, hep EtOAc). The solvent was removed to give the title compound as a white solid (2.6 g, 76%). MS (ESI): m/z [M+H]+ 484.2

Provenance & Evidence