[C@@H:1]1([NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:7].[CH2:9](O)[CH:10](O)[CH2:11][CH3:12]>C[C-]1C(C)=C(C)C(C)=C1C.C[C-]1C(C)=C(C)C(C)=C1C.[Cl-].[Cl-].[Cl-].[Cl-].[Ir+3].[Ir+3].C(=O)(O)[O-].[Na+]>[CH2:10]([C@@H:11]1[CH2:12][NH:8][C@@H:1]2[C@H:2]([CH2:3][CH2:4][CH2:5][CH2:6]2)[NH:7]1)[CH3:9]Dichloro(pentamethylcyclopentadienyl)iridium (III) dimer (70 mg, 0.090 mmol) and sodium bicarbonate (73 mg, 0.87 mmol) were added to an aqueous (20 mL) solution of trans-cyclohexane-1,2-diamine (2.00 g, 17.5 mmol) and (±)-1,2-butanediol (1.69 mL, 18.4 mmol) with stirring at room temperature. Degassing and argon substitution were repeated 3 times, and the mixture was then stirred for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (methylene chloride/methanol) to obtain (2R*,4aS*,8aS*)-2-ethyldecahydroquinoxaline (2.03 g, yield: 69%) in a yellow solid form.
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