1-Octene → HCID 67032429, compound

Participants

Reaction Steps

To a solution of 1-octene (2.12 mL, 13.5 mmol) in THF (50 mL) was added 9-BBN (4.3 g, 17.6 mmol), at 0° C. The reaction mixture was allowed to warm to RT and stirred overnight. Subsequently, K3PO4 (7.6 g, 35.8 mmol) was added, followed, after 45 minutes, by 4-benzyl-6-(4-bromo-phenyl)-morpholine (3.0 g, 9 mmol), palladium(II) acetate (80 mg; 4 mol %), and dicyclohexyl-(2′,6′-dimethoxy-biphenyl-2-yl)-phosphane (296 mg; 8 mol %). The resulting mixture was heated under reflux for 2 hours. After cooling to RT the mixture was concentrated in vacuo, the residue dissolved in EtOAc, and washed with 5% aqueous NaHCO3 solution. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes, 1:1) to afford 4-benzyl-2-(4-octyl-phenyl)-morpholine (2.58 g).

Provenance & Evidence