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To a stirred solution of compound 21 (752 mg, 2.85 mmol) in anhydrous ethanol (30 mL) was added, under argon, hydrazine monohydrate (324 μL, 6.68 mmol). The mixture was refluxed for 1 h. After cooling to room temperature, the white precipitate was filtered and washed with ethanol (10 mL). The filtrate was evaporated under vacuum and the residue was chromatographed (Al2O3, CH2Cl2/EtOH/NH4OH, 80/19/1, v/v/v) to give compound 22 (213 mg, 1.59 mmol) as an orange-coloured oil. Yield 56%; Rf (Al2O3, CH2Cl2/EtOH/NH4OH, 80/19/1, v/v/) 0.41; IR (CCl4) ν 1034, 1453, 1684, 2700-3000 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.01 (t, 3H, J=7.1 Hz), 2.59 (m, 4H), 2.74 (td, 2H, 3JH-F=26.5 Hz, J=5.3 Hz), 2.78 (t, 2H, J=5.3 Hz), 4.30 (se, 2H), 4.46 (td, 2H, 2JH-F=47.5 Hz, J=5.0 Hz).

1. temperatureThe mixture was refluxed for 1 h
2. filtrationthe white precipitate was filtered
3. washwashed with ethanol (10 mL)
4. customThe filtrate was evaporated under vacuum
5. customthe residue was chromatographed (Al2O3, CH2Cl2/EtOH/NH4OH, 80/19/1, v/v/v)