反应详情

Lithium hexamethyldisilylazide (1.0 M in THF; 7.20 mL, 7.20 mmol) was added to solution of benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (2.0 g, 6.55 mmol) in tetrahydrofuran (30 mL) at −78° C. After 40 min, 2,3-dibromoprop-1-ene (0.70 mL, 7.20 mmol) was added. After 2 h, the reaction mixture was warmed to ambient temperature. After 18 h, the mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate (2×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (80% hexanes/ethyl acetate→40% hexanes/ethyl acetate) gave the title compound (603 mg). MS 424.0 (M).

1. waitAfter 2 h
2. waitAfter 18 h
3. customthe mixture was quenched with saturated ammonium chloride
4. extractionextracted with ethyl acetate (2×)
5. dry with materialThe combined organic extracts were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by silica gel chromatography (80% hexanes/ethyl acetate→40% hexanes/ethyl acetate)