Ethyl (3R)-2-azido-4,4,4-trifluoro-3-methylbutanoate → Ethyl (3R)-4,4,4-trifluorovalinate

Participants

Reaction Steps

32.8 g of crude ethyl (3R)-2-azido-4,4,4-trifluoro-3-methylbutanoate (diastereomer mixture) were dissolved in 110 ml of ethanol and, after inertizing with argon, 6.98 g of palladium on carbon (5%) were added. The mixture was stirred overnight at standard pressure under an atmosphere of hydrogen, with the reaction vessel repeatedly being vented and filled with fresh hydrogen. The reaction mixture was then filtered off through Celite, the filter residue was washed with 50 ml of ethanol and the filtrate was concentrated under reduced pressure (up to about 20 mmHg). The slightly yellowish liquid that remained was briefly freed from residual solvent under high vacuum. This gave 23.5 g of the target compound as an about 70% pure crude product which was not purified any further (yield over three steps about 38% of theory).

Provenance & Evidence