cis-1,2,3,6-Tetrahydrophthalimide → (3aR,7aS)-rel-2,3,3a,4,7,7a-Hexahydro-1H-isoindole

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A suspension of lithium aluminum hydride (21.4 g, 0.562 mol) in THF (700 mL) at room temperature was treated with cis-1,2,3,6-tetrahydrophthalimide (Aldrich; 37 g, 0.245 mol) in small portions. The reaction mixture was stirred at 60° C. overnight then cooled to room temperature and quenched carefully by the sequential addition of water (22 mL), THF (22 mL), 15% aqueous KOH (22 mL), and water (80 mL). The mixture was diluted with diethyl ether (100 mL), stirred at room temperature for 1 hour, and then filtered (methylene chloride wash). The filtrate was concentrated under reduced pressure to provide the title compound as an oil (26.1 g). 1H NMR (CDCl3, 300 MHz) δ 1.76–2.02 (m, 2H), 2.10–2.33 (m, 3H), 2.34–2.56 (m, 2H), 2.61–2.79 (m, 2H), 2.87–3.17 (m, 2H), 5.53–6.03 (m, 2H); MS (DCI/NH3) m/z 124 (M+H)+.

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