Triethylamine → HCID 21073532, compound

Participants

Reaction Steps

To a solution of 4-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-pentanal (450 mg, crude) in DCE (10 mL) was added 2,3-dichlorophenyl-piperazine hydrochloride (495 mg, 1.85 mmol) followed by Et3N (0.55 mL, 3.96 mmol). The mixture was stirred for 10 min and then powdered NaBH(OAc)3 (534 mg, 2.52 mmol) was added. The reaction was stirred at room temperature for 2 h and then quenched with saturated NaHCO3. The mixture was extracted with EtOAc (2×). The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated to give a foam. Purification by liquid chromatography (4% MeOH/CH2Cl2) gave the title compound as a white foam (507 mg, 1.09 mmol, 61%). MS: APCI: M+1: 463.1 (Exact Mass: 462.16). The enantiomers were separated by chiral HPLC (Chiralcel OD).

Provenance & Evidence