Sodium Iodide → HCID 18461084, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate (68 mg, 0.249 mmol) in pyridine (2.5 ml) was added NaI (746 mg, 4.98 mmol). The reaction mixture was then reflux at 120° C. for 7.5 hr. The reaction mixture was concentrated and placed under vacuum. The residue was then partitioned between EtOAc and water. The aqueous phase was separated and extracted with EtOAc. All organic phases were combined, washed with saturated aqueous Na2S2O3 solution, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-40% EtOAc/Hex to give the product 8-benzyl-8-azabicyclo[3.2.1]octan-2-one (39.4 mg, 0.183 mmol) as a syrup. Anal. Calcd. for C14H17NO m/z 215.1, found: 216.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.21 (5 H, m), 3.68 (2 H, s), 3.36 (2 H, d, J=5.5 Hz), 2.45-2.28 (2 H, m), 2.27-2.16 (3 H, m), 1.81-1.70 (3 H, m).

Provenance & Evidence