Cyclopentanol → cis-Phenylmethyl 5-{[(cyclopentyloxy)carbonyl]amino}-2-methyl-1-piperidinecarboxylate

Participants

Reaction Steps

To a mixture of cis-6-methyl-1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinecarboxylic acid (200 mg, 0.721 mmol), cyclopentyl alcohol (1.5 mL, 16.51 mmol), and triethylamine (0.151 mL, 1.082 mmol) was added slowly diphenyl azidophosphate (dppa) (0.171 mL, 0.793 mmol), and the reaction mixture was stirred at room temperature for 15 minutes, and then at 125° C. After 4 hr, the reaction was diluted with EtOAc (40 mL) and washed with water. The organic was then dried over MgSO4, filtered, concentrated and purified with Biotage SNAP 10 g column with gradient of 0 to 50% EtOAc in hexane over 35 minutes to afford the title compound (160 mg) as a clear oil. LC-MS (ES) m/z=361 [M+H]+.

Provenance & Evidence