tert-Butanol → tert-Butyl {1-[(4-cyanopiperidin-1-yl)carbonyl]-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl}carbamate

Participants

Reaction Steps

18 g of molecular sieves 4 Å, 3.2 ml (2.3 g, 23 mmol) of triethylamine and 4.6 ml (5.8 g, 21 mmol) of diphenyl phosphorazidate were added to a solution of 7.90 g (19.3 mmol) of the carboxylic acid from Example 67A in 350 ml of tert-butanol, and the mixture was stirred under reflux overnight. The molecular sieves were then filtered off and washed repeatedly with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue was taken up in ethyl acetate and then washed with 2N hydrochloric acid, saturated aqueous sodium bicarbonate solution and water. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 8.34 g with a purity of 91% (82% of theory)

Provenance & Evidence