反应详情

(5R)-3-(4-(1-Benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluorophenyl)-5-hydroxymethyl-oxazolidin-2-one (2.92 g, 7.3 mM; WO 97-30995) was stirred in tetrahydrofuran (60 ml), and 3H-oxazol-2-one (0.69 g, 8.12 mM) and tributylphosphine (1.77 g, 8.75 mM) were added. The mixture was stirred at 0° under nitrogen, and 1,1′-azodicarbonyldipiperidine (2.06 g, 8.18 mM) was added portionwise. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The precipitate was filtered off and solvent removed. The resulting oil was dissolved in dichloromethane (30 ml), stirred at 0° for 30 minutes, and further precipitate removed. The filtrate was purified by MPLC on silica eluting with a gradient from 60 to 80% ethyl acetate in isohexane, to give a mixture of starting material and product, which was rechromatographed eluting with 3% MeOH in dichloromethane to give the title compound as a white solid (30 mg).

1. stirringstirred overnight
2. filtrationThe precipitate was filtered off
3. customsolvent removed
4. dissolutionThe resulting oil was dissolved in dichloromethane (30 ml)
5. stirringstirred at 0° for 30 minutes
6. customfurther precipitate
7. customremoved
8. customThe filtrate was purified by MPLC on silica eluting with a gradient from 60 to 80% ethyl acetate in isohexane
9. customto give
10. additiona mixture of starting material and product, which
11. customwas rechromatographed
12. washeluting with 3% MeOH in dichloromethane