tert-Butanol → benzyl (2S,5R)-5-((tert-butoxycarbonyl)amino)-2-methylpiperidine-1-carboxylate

Participants

Reaction Steps

cis-6-methyl-1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinecarboxylic acid (2.62 g, 9.45 mmol) was dissolved in t-butyl alcohol (20 mL, 212 mmol) (anhydrous) in a 40 mL vial. Triethylamine (1.975 mL, 14.17 mmol) was added, followed by the slow addition of diphenyl azidophosphate (dppa) (1.87 mL, 8.65 mmol) at room temperature. The reaction was stirred at room temperature for 30 minutes, and then heated at 100° C. overnight. The reaction mixture was concentrated, and then redissolved with 150 mL of EtOAc. The resulting organic mixture was washed with water (50 mL), brine, dried (Na2SO4), filtered, and concentrated. The resulting clear oil was purified in 50 g Biotage SNAP column with gradient of 0 to 50% of EtOAc in Hexane over 40 minutes to afford the title compound (1.06 g) as a clear oil. LC-MS (ES) m/z=349 [M+H]+.

Provenance & Evidence