反应详情

A solution of Example 173B (127 mg, 0.3 mmol) in dioxane (6 mL) and water (2 mL) was treated with OSO4 (2.5% wt in t-butanol, 0.5 mL), stirred for 8 minutes at ambient temperature, treated with NaIO4 (128 mg, 0.6 mmol), stirred for 30 minutes, diluted with brine, and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4), filtered, and concentrated. This concentrate was dissolved in absolute ethanol (5 mL) and THF (5 mL), treated with NaBH4 (7 mg), stirred for 30 minutes, treated with brine (10 mL), and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography with 45% ethyl acetate/hexanes to provide the desired product (71 mg, 56.7%). 1H NMR (DMSO-d6) δ 2.05 (s, 3H), 4.42 (d, 2H), 5.12 (t, 1H), 5.24 (s, 2H), 6.84 (d, 1H), 7.35-7.46 (m, 8H), 7.70-7.75 (m, 2H), 9.81 (s, 1H); MS (ESI(−)) m/e 428 (M−H)−.

1. stirringstirred for 30 minutes
2. extractionextracted with ethyl acetate
3. dry with materialThe ethyl acetate solution was dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThis concentrate was dissolved in absolute ethanol (5 mL)
7. additionTHF (5 mL), treated with NaBH4 (7 mg)
8. stirringstirred for 30 minutes
9. additiontreated with brine (10 mL)
10. extractionextracted with ethyl acetate
11. dry with materialThe ethyl acetate solution was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated
14. customThe residue was purified by flash column chromatography with 45% ethyl acetate/hexanes