反应详情

To an ice-cold solution of the product of Step H (426 g, 1.57 mol) and acetone (8.1 L) was added Jones reagent (710 mL) over 1 h 20 min. The resulting suspension was stirred at rt for 1 h, after which isopropyl alcohol (40 mL) was added, and the reaction stirred for 25 min at rt. Water was added, and the water/acetone was decanted off and evaporated. The insoluble material was dissolved separately in water and extracted with CH2Cl2. The green water/acetone concentrate was extracted with CH2Cl2 and the combined organic extracts were washed with brine, diluted with water and EtOAc and the organic layer was dried with Na2SO4. The organic layer was filtered, concentrated and the product was crystallized from MeCN, and the product of Step I was isolated by filtration as a white solid. 1H NMR (400 MHz, DMSO-d6) d=12.39-12.59 (m, 1H), 6.85-7.02 (m, 1H), 4.28 (d, J=5.4 Hz, 1H), 3.89-3.97 (m, 1H), 3.79-3.85 (m, 1H), 3.43-3.51 (m, 1H), 3.30-3.36 (m, 1H), 2.35-2.42 (m, 1H), 1.90 (d, J=11.0 Hz, 3H), 1.59-1.70 (m, 1H), 1.42-1.50 (m, 1H), 1.37 (s, 9H). Elemental anal calc for C13H21NO5: C, 57.55; H, 7.80; N, 5.16. Found: C, 57.34; H, 8.18; N, 5.08 mp: 147.4-149.1° C.

1. stirringthe reaction stirred for 25 min at rt
2. customthe water/acetone was decanted off
3. customevaporated
4. dissolutionThe insoluble material was dissolved separately in water
5. extractionextracted with CH2Cl2
6. concentrationThe green water/acetone concentrate
7. extractionwas extracted with CH2Cl2
8. washthe combined organic extracts were washed with brine
9. additiondiluted with water and EtOAc
10. dry with materialthe organic layer was dried with Na2SO4
11. filtrationThe organic layer was filtered
12. concentrationconcentrated
13. customthe product was crystallized from MeCN