Tert-Butylamine → tert-butyl (2R,5S)-2-[(R)-[6-(tert-butylamino)pyridin-3-yl]{[tert-butyl(dimethyl)silyl]oxy}methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl (2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(1-oxidopyridin-3-yl)methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate (0.049 g, 0.087 mmol) in trifluorotoluene (2 mL) was cooled to 0° C. Tert-butylamine (0.046 mL, 0.44 mmol) was added, followed by p-toluenesulfonic anhydride (0.057 g, 0.18 mmol). After 1 hour, the reaction was diluted with EtOAc (50 mL) and washed with water (15 mL) and brine (15 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography with 0-45% EtOAc/hexanes to afford 47 mg of impure tert-butyl (2R,5S)-2-[(R)-[6-(tert-butylamino)pyridin-3-yl]{[tert-butyl(dimethyl)silyl]oxy}methyl]-5-[4-(methoxycarbonyl)benzyl]pyrrolidine-1-carboxylate. LC-MS=6123 (M−H)+.

Provenance & Evidence