HCID 86616002, compound → 952714-27-1

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]+.

1. customA 2 L Parr bottle was flushed with N2 and 9.374 g (0.10 g/mmol) of 10% Pd/C
2. additionwas carefully added to the flask
3. additionThen, 50 mL of anhydrous MeOH was added
4. additionwas added to the flask
5. customThe Parr bottle was flushed with more N2
6. customcapped
7. filtrationby filtering through a 1-inch pad of the Celite® reagent
8. washwashing with 1.5-2 L of MeOH
9. concentrationconcentrated in vacuo

ORD record

ord-d7cbe72c3f784ecf9e9e9f6864540078

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550629B2