Sodium bis(trimethylsilyl)amide → 3-(3-Cyano-phenyl)-2-methyl-propionic acid methyl ester

Participants

Reaction Steps

To a solution of 3-(3-cyano-phenyl)-propionic acid methyl ester of Step A (220mg, 1.16 mmol) in THF (5 mL) at -78° C. was added sodium bis(trimethylsilyl)amide (1M in THF, 1.2 mL, 1.2 mmol). The reaction was stirred for 0.5 h and Mel (0.08 mL, 1.28 mmol) was added. After 1 h, a solution of saturated NaHCO3:water (1:1) was added and the reaction was warmed to room temperature. The aqueous solution was washed with CH2Cl2 (3×) and the combined organic solutions were dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (6:1 hexanes:EtOAc) provided the title compound of Step B as a colorless oil (62 mg). 1H NMR (400 MHz, CDCl3) δ 7.50-7.34 (m, 4H), 3.62 (s, 3H), 3.01 (m, 1H), 2.71 (m, 2H), 1.16 (d, 3H).

Provenance & Evidence