[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]2[CH2:6][NH:7][CH2:8][CH2:9][CH:4]2[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>CC(C)=O.O>[C:13]([O:12][C:10]([N:1]1[CH:5]2[CH2:6][N:7]([CH2:24][CH2:25][CH2:26][Cl:27])[CH2:8][CH2:9][CH:4]2[CH2:3][CH2:2]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]To a solution of tert-butyl octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (1.21 g) in acetone (15 mL) was added K2CO3 (3.00 g) and 1-bromo-3-chloropropane (1.6 mL). The reaction mixture was heated to reflux for 7 h, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) CH2Cl2/MeOH) to afford the title compound as pale yellow liquid (1.20 g, 75.00%).
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