N,N'-Dimethylethylenediamine → HCID 69057399, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-trans-tert-butyl 8-ethyl-6-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate from Example 74, Part A (50 mg, 0.15 mmol) in 2 mL of degassed toluene was added copper (I) iodide (2.1 mg, 0.011 mmol), potassium phosphate (70 mg, 0.33 mmol), iodobenzene (0.020 mL, 0.18 mmol) and N,N′-dimethylethylenediamine (0.0025 mL, 0.022 mmol). The mixture was stirred at 110° C. for 2 days. The reaction was cooled and quenched with 1N HCl and diluted with ethyl acetate. The organics were washed sequentially with sat'd aq. NaHCO3, and brine, dried (MgSO4), and concentrated. The residue was purified by flash chromatography (elution with 6:1 hexane/EtOAc) to afford 25 mg (41%) of the title compound as an oil. LRMS (ESI): 407.3 (M+H)+.

Provenance & Evidence