Reaction Steps
[(Isoquinoline-1-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carboxylic acid methyl ester, 13, (1.62 g, 4.1 mmol) are added to 20 mL of THF/H2O (3:1). Lithium hydroxide (0.25 g) is added and the reaction stirred at room temperature for 18 hours then diluted with ethyl acetate (100 mL). The organic layer is washed with 1N HCl, brine, and dried over MgSO4. Solvent is removed in vacuo to afford 1.41 g (90% yield of the desired product as an oil, which is used without further purification. 1H NMR (CDCl3): δ 9.30 (d, J=8.5 Hz, 1H), 8.92 (d, J=7.7 Hz, 1H), 8.53 (d, J=7.8 Hz, 1H), 7.93 (m, 2H), 7.83–7.71 (m, 2H), 5.88 (m, 1H), 5.75 (m, 1H), 5.50 (m, 1H), 4.70 (d, 7.4 Hz, 1H), 4.37 (m, 1H), 3.10–2.91 (m, 2H), 2.44 (m, 3H), 2.21 (m, 1H), 2.03 (m, 2H), 13C NMR (CDCl3): δ 173.5, 171.9, 165.0, 148.1, 139.3, 137.9, 137.6, 131.7, 129.8, 129.5, 127.7, 127.3, 126.9, 125.9, 125.2, 61.4, 59.5, 50.9, 33.9, 33.3, 32.5, 26.0. ESI MS 380.15(M+H).
