[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][CH2:17][F:18].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:16][CH2:17][F:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]A mixture of 1-tert-butoxycarbonylhomopiperazine (800 mg, 3.99 mmol), 1-bromo-2-fluoroethane (0.46 mL, 11.98 mmol) and potassium carbonate (1.10 g, 7.98 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred overnight at 70° C. and was cooled to room temperature. The reaction mixture was filtered through a Celite pad, and the filtrate was evaporated to dryness under vacuum to afford yellowish oil. The crude product was purified by MPLC on silica gel (3% MeOH in CHCl3) to afford the titled compound (653 mg, 67%) as a pale yellow oil.
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