反应详情

Lithium hexamethyldisilylazide (1.0 M in THF; 18.0 mL, 18.0 mmol) was added to a solution of benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (5.0 g, 16.4 mmol) in tetrahydrofuran (90 mL) at −78° C. After 40 min, 3-bromo-2-methylprop-1-ene (1.81 mL, 18.0 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 16 h, the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. Purified by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate) to give the title compound (2.88 g). MS 360.2 (M+1).

1. waitAfter 16 h
2. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
3. extractionextracted with ethyl acetate (2×)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customPurified by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate)