Sodium Hydroxide → (3R)-N-[(Allyloxy)carbonyl]-4,4,4-trifluorovaline

Participants

Reaction Steps

6.50 g (22.9 mmol) of ethyl (3R)—N-[(allyloxy)carbonyl]-4,4,4-trifluorovalinate (diastereomer mixture) were dissolved in a mixture of in each case 28 ml of THF, ethanol and water, and 13.77 g (344 mmol) of sodium hydroxide were added at 0° C. Ice-cooling was removed and the reaction mixture was stirred at RT overnight. The mixture was then added to water, acidified with semiconcentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with sat. sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. This gave 4.39 g of the target product which was not purified any further (75% of theory, diastereomer ratio about 2.5:1).

Provenance & Evidence