HCID 86616002, compound → (2S)-2-amino-4,4,4-trifluoro-3-(trifluoromethyl)butan-1-ol hydrochloride

Participants

Reaction Steps

A 2 L Parr bottle was flushed with N2 and 9.374 g (0.10 g/mmol) of 10% Pd/C was carefully added to the flask. Then, 50 mL of anhydrous MeOH was added and the flask was carefully swirled. A solution of 36.136 g (98.3 mmol, 1.0 equiv) of (2S)-4,4,4-trifluoro-2-{[(1R)-1-phenylethyl]amino}-3-(trifluoromethyl)butan-1-ol hydrochloride salt dissolved in 50 mL of MeOH was added to the flask. The Parr bottle was flushed with more N2, and then capped. The heterogeneous reaction mixture was hydrogenated at 45 psi for 2 h. The reaction was checked for completion by 1H NMR. The reaction was worked up by filtering through a 1-inch pad of the Celite® reagent and washing with 1.5-2 L of MeOH. The filtrates were combined and concentrated in vacuo to give 28.56 g (100%) of (2S)-2-amino-4,4,4-trifluoro-3-(trifluoromethyl)butan-1-ol hydrochloride salt as a cream-colored solid. Further purification by triturating with 80 mL of 1:1 hexane:Et2O can also be performed. Mass Spectrum (+ESI): 212.1 [M+H]+.

Provenance & Evidence