Hydrochloric Acid → 3,3,3-Trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine

Participants

Reaction Steps

A solution of lithium borohydride (2M THF, 19.8 mL) was added to a solution of 2-amino-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (5 g, 19.8 mmol), prepared as described (J. Med Chem. 1981, 24, 1043-1047), in THF (80 mL) at 25° C. and was stirred for 4 h. 2M HCl was added to the reaction mixture very carefully until a pH less than 2. The organic solvent was removed in vacuo and the aqueous layer was neutralized with sat NaHCO3 until pH=7. The aqueous layer was extracted with EtOAc (2×50 mL) and the organic extracts were dried over Na2SO4 and concentrated to provide 3,3,3-trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine as a yellow oil (3.2 g, 77% yield). The crude oil was of sufficient purity to utilize in the subsequent reaction.

Provenance & Evidence