反应详情

tert-Butyl [(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]methylcarbamate (1.8 g, 6.1 mmol) was dissolved in a mixture of acetone (32 mL), tert-butanol (16 mL) and water (8 mL). The solution was stirred at room temperature during addition of OsO4 (0.64 mL of 2.5% in tert-butanol, 0.06 mmol) and 4-methylmorpholine N-oxide (3.2 g, 27 mmol). The mixture was stirred at room temperature for 4 h. A saturated aqueous solution of sodium bisulfite (60 mL) was added and the mixture stirred for 20 min and then diluted with water (100 mL). The solution was extracted twice with CH2Cl2 and the combined organic solutions were washed with brine. The solvent removed by evaporation and the residue (2.4 g) was dissolved in a mixture of THF (28 mL) and water (12 mL) whereupon sodium periodate (1.44 g, 6.7 mmol) was added. The solution was stirred at room temperature for 4.5 h and then diluted with water and brine. The mixture was extracted twice with CH2Cl2 and the combined organic solutions were dried over MgSO4. The solvent was removed by evaporation and there was obtained 1.58 g (87%) of tert-butyl [(2S)-2-(4-fluorophenyl)-4-oxobutyl]methylcarbamate. 1H NMR (500 MHz, CDCl3): 1.4 (s, 9H), 2.6-2.8 (m, 5H), 3.2-3.6 (cm, 3H), 7.0 (m, 2H), 7.1 (b, 2H), 9.7 (s, 1H).

1. stirringthe mixture stirred for 20 min
2. extractionThe solution was extracted twice with CH2Cl2
3. washthe combined organic solutions were washed with brine
4. customThe solvent removed by evaporation
5. additionwas added
6. stirringThe solution was stirred at room temperature for 4.5 h
7. extractionThe mixture was extracted twice with CH2Cl2
8. dry with materialthe combined organic solutions were dried over MgSO4
9. customThe solvent was removed by evaporation