反应详情

To solution of 49 (1.00 g, 2.56 mmol) in MeOH (20 ml) was added 10% Pd/C (200 mg) and the mixture was stirred under H2 for 2 hours. The mixture was filtered through a 0.45 μm PTFE filter and the solvent removed in vacuo to yield a colorless oil. This oil was dissolved in CH2Cl2 (25 mL) and DIEA (660 μl, 3.79 mmol) and p-anisoyl chloride (480 mg, 2.8 mmol) were added. The solution was stirred at room temperature under N2 for 18 hours. The solvent was removed in vacuo and the oil dissolved in EtOAc. The organic phase was washed with 0.5N NaHSO4 (2×), water, saturated NaHCO3 (2×) and brine. The organic phase was dried over Na2SO4, filtered and evaporated to give a white solid which was purified by flash column chromatography, eluting with CH2Cl2/MeOH (99/1 to 98/2%) to give the title compound as a white solid (655 mg, 65% yield). 1H-NMR (500 MHz, CDCl3) δ 1.47 (s, 9H), 1.68-2.24 (m, 5H), 1.80 (d, 6H), 3.55-3.68 (m, 1H), 3.72-3.93 (m, 1H), 3.84 (s, 3H), 4.43-4.55 (m, 1H), 6.90 (d, 2H), 7.60 (br s, 1H), 7.77 (d, 2H). Analytical HPLC (C18 column) 8.98 min.

1. filtrationThe mixture was filtered through a 0.45 μm PTFE
2. filtrationfilter
3. customthe solvent removed in vacuo
4. customto yield a colorless oil
5. stirringThe solution was stirred at room temperature under N2 for 18 hours
6. customThe solvent was removed in vacuo
7. dissolutionthe oil dissolved in EtOAc
8. washThe organic phase was washed with 0.5N NaHSO4 (2×), water, saturated NaHCO3 (2×) and brine
9. dry with materialThe organic phase was dried over Na2SO4
10. filtrationfiltered
11. customevaporated
12. customto give a white solid which
13. customwas purified by flash column chromatography
14. washeluting with CH2Cl2/MeOH (99/1 to 98/2%)