反应详情

An 25-mL round bottom flask containing a stir bar was charged with Pd2(dba)3 (00.01 equiv., 0.0154 mmol, 14 mg.), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 1 (0.05 equiv., 0.077 mmol, 36.7 mg), 2-(4-bromo-2-methyl-phenyl)-8-oxa-aza-spiro[4.5]decan-1-one (0.50 g, 1.54 mmol, 1 equiv.), and sodium t-butoxide (2.5 equiv., 3.85 mmol, 370 mg.), and piperidin-4-ol (1.5 equiv., 2.3 mmol, 234 mg). The vial was capped with a rubber septum, evacuated and backfilled with N2. To this vial was introduced 8 mL of anhydrous toluene. The reaction was heated in an oil bath set at 90° C. for 2 h, allowed to cool down to room temperature and quenched with water (2 mL). The two layers were separated and the aqueous layer was extracted with DCM (3×10 mL). The combined DCM extracts were washed with sodium bicarbonate (50 mL), and brine (50 mL), dried (anhydrous potassium carbonate), filtered, and concentrated. The crude product was purified by a silica gel column to give 75.1 mg (14% yield) of the title compound as a light yellow solid after standing.

1. additionAn 25-mL round bottom flask containing a stir bar
2. customThe vial was capped with a rubber septum
3. customevacuated
4. additionTo this vial was introduced 8 mL of anhydrous toluene
5. temperatureThe reaction was heated in an oil bath
6. customquenched with water (2 mL)
7. customThe two layers were separated
8. extractionthe aqueous layer was extracted with DCM (3×10 mL)
9. washThe combined DCM extracts were washed with sodium bicarbonate (50 mL), and brine (50 mL)
10. dry with materialdried (anhydrous potassium carbonate)
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude product was purified by a silica gel column