反应详情

温度

90 °C

To a stirred solution of tert-butyl [1-(hydroxymethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (as obtained in step VI preparation 3) (0.67 g, 2.5 mmol) in toluene (10 mL) was added phthalimide (0.52 g, 3.5 mmol), triphenylphosphine (1.05 g, 4.0 mmol), and diisopropylazodicarboxylate (0.8 mL, 4.0 mmol). The reaction mixture was heated to 90° C. for 4 h. The volatiles were removed under reduced pressure and the residue was purified by column chromatography to obtain tert-butyl [2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]carbamate (0.45 g) as a viscous liquid in 46% yield. m/z (M+1) 397; 1H NMR (CDCl3) 300 MHz δ 7.90-7.80 (m, 2H), 7.77-7.68 (m, 2H), 4.75 (s (br), 1H), 3.60 (s, 2H), 2.47-2.35 (m, 1H), 2.36-2.29 (m, 1H), 2.02-1.84 (m, 4H), 1.77-1.65 (m, 2H), 1.64-1.35 (m, 5H), 1.41 (s, 9H), 1.34-1.24 (m, 1H).

1. customThe volatiles were removed under reduced pressure
2. customthe residue was purified by column chromatography