反应详情

温度

-78 °C

SEM dilactam 14e (0.250 g, 0.196 mmol, 1.0 eq.) was solubilised in THF (13 mL) and cooled to −78° C. under a nitrogen atmosphere. Super hydride solution (0.40 mL, 0.401 mmol, 2.04 eq.) was added dropwise over 5 min. After 20 min an aliquot was washed with water for LCMS and TLC analysis. After 30 mins water (30 mL) was added and the cold bath removed. The organic layer was extracted with EtOAc (2×40 mL) and the combined organic extracts washed with brine (40 mL), dried with MgSO4, filtered and removed under reduced pressure. The crude product was dissolved in MeOH (13 mL), DCM (7 mL) and water (1.7 mL) and enough silica gel to form a thick stirring suspension. After 5 days the suspension was filtered through a sintered funnel and washed with DCM/MeOH 9:1 (˜200 mL) until complete elution of product. The organic layer was washed with brine (2×70 mL), dried with MgSO4, filtered and the solvent removed under reduced pressure. Purification by flash chromatography (silica gel, CHCl3 100 to 96:4 v/v CHCl3/MeOH) afforded the product as a pale yellow solid (0.090 g, 47%). LC/MS (2.112 min (ES+)), m/z: 981.0 [M+H]+.

1. washAfter 20 min an aliquot was washed with water for LCMS and TLC analysis
2. additionAfter 30 mins water (30 mL) was added
3. customthe cold bath removed
4. extractionThe organic layer was extracted with EtOAc (2×40 mL)
5. washthe combined organic extracts washed with brine (40 mL)
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. customremoved under reduced pressure
9. dissolutionThe crude product was dissolved in MeOH (13 mL)
10. customDCM (7 mL) and water (1.7 mL) and enough silica gel to form a thick stirring suspension
11. filtrationAfter 5 days the suspension was filtered through a sintered funnel
12. washwashed with DCM/MeOH 9:1 (˜200 mL) until complete elution of product
13. washThe organic layer was washed with brine (2×70 mL)
14. dry with materialdried with MgSO4
15. filtrationfiltered
16. customthe solvent removed under reduced pressure
17. customPurification by flash chromatography (silica gel, CHCl3 100 to 96:4 v/v CHCl3/MeOH)