反应详情

The above crude thiomethyl compound of Example 4 was dissolved in absolute ethanol (340 mL) under argon and mixed with Raney nickel (17 teaspoons) freshly washed with water and ethanol (3 times). The resulting mixture was stirred vigorously at room temperature for 1 hours. Stirring was stopped, and the liquid layer was removed by decanting. The catalyst was then washed with ethanol (250 mL) and dichloromethane (250 mL). The liquid was removed by decanting in each case. The combined liquid layer was concentrated in vacuo. The residue was dissolved in methyl t-butyl ether (300 mL), washed with water (200 mL), and brine (200 mL) and dried over anhydrous sodium sulfate. Removal of solvent in vacuo afforded the crude product as a colorless oil (14.3 g, 83%): 1H NMR (CDCl3) δ1.26 (t, J=7.2 Hz, 3H), 1.80 (m, 1H), 2.00 (m, 1H), 2.70-2.95 (m, 2H), 3.50 (m, 3H), 3.80-3.85 (m, 1H), 4.15 (m, 4H), 6.76 (d, J=8.4 Hz, 1H), 6.98 (s,1H), 7.02 (d, J=8.7 Hz, 1H); CI-MS m/z 346 (M+H+). The crude was used for next step without further purification.

1. washfreshly washed with water and ethanol (3 times)
2. stirringStirring
3. customthe liquid layer was removed
4. customby decanting
5. washThe catalyst was then washed with ethanol (250 mL) and dichloromethane (250 mL)
6. customThe liquid was removed
7. customby decanting in each case
8. concentrationThe combined liquid layer was concentrated in vacuo
9. dissolutionThe residue was dissolved in methyl t-butyl ether (300 mL)
10. washwashed with water (200 mL), and brine (200 mL)
11. dry with materialdried over anhydrous sodium sulfate
12. customRemoval of solvent in vacuo