Oxygen → HCID 58109464, compound

Participants

Reaction Steps

(R)-6-allyl-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (55 mg, 0.13 mmol), PdCl2 (6 mg, 0.3 equiv.), and CuCl (26 mg, 2.3 equiv.) were mixed with DMF (2 mL) and water (˜250 μL). A balloon of oxygen was attached to the flask and the mixture was stirred vigorously overnight. LC-MS found the reaction completed. The mixture was quenched by satd aq NH4Cl solution (2 mL), diluted with EtOAc (20 mL), washed by brine (7 mL), dried over Na2SO4. After filtration and concentration, the residue was purified by preparative HPLC to afford (S)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-oxopropyl)-1,3-oxazinan-2-one (49 mg, 86% yield). LC-MS (3 min) tR=1.76 min, m/z=434, 436 (M+1).

Provenance & Evidence