C([O-])([O-])=O.[Cs+].[Cs+].[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1.Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][CH:22]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([NH:7][C@H:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:22][CH:23]=1A 5 ml vial was charged with Cs2CO3 (654 mg, 3.3 mmol) and was dried in vacuo at 60° C. for two hours. Palladium acetate (31.5 mg, 0.14 mmol), BI NAP (43 mg, 0.07 mmol) were added followed by anhydrous dioxane (2 ml). The mixture was sonicated for one hour after which tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate (186.3 mg, 1.0 mmol) and 4-chloroquinoline (163 mg, 1 mmol) dissolved in 2 ml anhydrous dioxane were added. The mixture was stirred at 100° C. overnight. The reaction mixture was purified directly by column chromatography (prepacked silica column, gradient heptan/ethyl acetate). 231 mg (0.68 mmol, 68%) of a solid were obtained. MS (APCI): m/z=314.0 [M+1]+.
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