Aluminium lithium hydride → (3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amine

Participants

Reaction Steps

tert-Butyl(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylcarbamate (59 mg, 0.187 mmol) from Step A was treated with lithium aluminum hydride (0.374 mmol) in tetrahydrofuran (0.5 mL). The reaction was stirred at room temperature for 1 hour and then heated to reflux for 2 hours. The reaction was cooled to room temperature and quenched with dropwise addition of saturated aqueous sodium sulfate (50 μL) to give a precipitate. The precipitate was washed with tetrahydrofuran, and then the solvent was removed to give (3aR,4S,6aS)-2-benzyl-N-methyloctahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.34-7.28 (m, 4H), 7.25-7.19 (m, 1H), 3.60-3.51 (m, 2H), 2.76 (q, J=5.6, 1H), 2.64 (d, J=15.7, 1H), 2.58-2.53 (m, 1H), 2.51-2.46 (m, 1H), 2.40-2.35 (m, 4H), 2.31-2.22 (m, 2H), 1.98-1.85 (m, 2H), 1.39 (dt, J=5.7, 10.6, 3H); MS (ESI+) m/z 231 (M+H)+.

Provenance & Evidence