3-Bromo-2-methyl-1-propene → HCID 67440198, compound

Participants

Reaction Steps

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).

Provenance & Evidence