反应详情

温度

0 °C

To a stirred solution of Intermediate 117 (7.3 g, 19.65 mmol) in DCM (180 mL) was added N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine (25.3 g, 117.89 mmol). Then it was cooled to 0° C. and trimethyloxonium tetrafluoroborate (8.72 g, 58.94 mmol) was added. The reaction was then stirred at rt for several hours until LCMS showed the starting material was all consumed. Then it was concentrated under reduced pressure. The residue was then taken up in 100 mL Et2O and filtered, washed with 100 mL Et2O. The organic layer was then washed with 10% citric acid, aq NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was then taken up in MeOH (180 mL), cooled to 0° C. and cerium(III) chloride (7.32 g, 19.65 mmol) was then added to give a clear solution. Then NaBH4 (0.743 g, 19.65 mmol) was added as solid, and the mixture was stirred from 0° C. to rt for 1 hr. The reaction mixture was concentrated in vacuo. The white solid was redissolved in 200 mL Et2O and washed with 10% citric acid, NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column (20-80% Hex/EA, 80 g) to afford the title compound (6.20 g, 81%) as a colorless oil (−3.8:1 mixture of 2 diastereomers).

1. concentrationThen it was concentrated under reduced pressure
2. filtrationfiltered
3. washwashed with 100 mL Et2O
4. washThe organic layer was then washed with 10% citric acid, aq NaHCO3, brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. temperaturecooled to 0° C.
9. customto give a clear solution
10. stirringthe mixture was stirred from 0° C. to rt for 1 hr
11. concentrationThe reaction mixture was concentrated in vacuo
12. dissolutionThe white solid was redissolved in 200 mL Et2O
13. washwashed with 10% citric acid, NaHCO3, brine
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated
17. customThe residue was purified by silica gel column (20-80% Hex/EA, 80 g)