N-(Diphenylmethylene)glycine tert-butyl ester → HCID 68551405, compound

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Reaction Conditions

Reaction Steps

660 mg of N-(diphenylmethylene)glycine tert-butyl ester (2.23 mmol, 1.0 equiv.) were dissolved in 15 ml of dry THF and cooled to 0° C. under argon. Then 2.23 ml of 1 M lithium hexamethyldisilazane (LiHMDS) solution in THF were added dropwise, and the mixture was stirred at 0° C. for 15 min. Subsequently, 642 mg of tert-butyl (5-bromomethylpyridin-2-yl)-carbamate (2.23 mmol, 1.0 equiv.) were added, and the mixture was stirred at 0° C. for 2 h. The mixture was quenched with 18 ml of sat. citric acid and stirred at RT for 1 h. The mixture was extracted with ethyl acetate (2×30 ml), and the organic phases were washed with 50 ml of 1 M HCl. The aqueous phases were combined and adjusted to pH 10 with 2M NaOH and then extracted 3× with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on silica gel with heptane/ethyl acetate mixtures as eluent. 600 mg (80% yield) of the title compound were obtained as a colorless solid.

Provenance & Evidence