反应详情

温度

0 °C

To a solution of (S,E)-N-(2-(tert-butyldimethylsilyloxy)propylidene)-1-(4-methoxyphenyl)methanamine (3.38 g, 11 mmol) in dichloromethane (90 mL) was added TMSOTf (2.2 mL, 12.1 mmol) and tert-butyldimethyl(4-methylpenta-1,3-dien-2-yloxy)silane (9.35 g, 44 mmol) at 0° C. After stirring for 2 days at 0° C., the reaction mixture was poured into aq. NaHCO3 solution (100 mL), followed by extraction with dichloromethane (100 mL×2). The combined organic layers were dried over MgSO4, and the solvent was evaporated. The residue was dissolved in THF (60 mL) and then 41.8 mL of TBAF (1 M in THF, 41.8 mmol) was added to the solution. The mixture was stirred for 12 h, quenched with water (100 mL), extracted with dichloromethane (100 mL×2), and the combined extracts were dried over Na2SO4. After the solvent was concentrated in vacuo, the product was purified by column chromatography (Et2O/Heptane) to give 1.3 g (41%) of (S)-6-((S)-1-hydroxyethyl)-1-(4-methoxybenzyl)-2,2-dimethylpiperidin-4-one and 1.0 g (31%) of (R)-6-((S)-1-hydroxyethyl)-1-(4-methoxybenzyl)-2,2-dimethylpiperidin-4-one.

1. extractionfollowed by extraction with dichloromethane (100 mL×2)
2. dry with materialThe combined organic layers were dried over MgSO4
3. customthe solvent was evaporated
4. dissolutionThe residue was dissolved in THF (60 mL)
5. stirringThe mixture was stirred for 12 h
6. customquenched with water (100 mL)
7. extractionextracted with dichloromethane (100 mL×2)
8. dry with materialthe combined extracts were dried over Na2SO4
9. concentrationAfter the solvent was concentrated in vacuo
10. customthe product was purified by column chromatography (Et2O/Heptane)