Hydrochloric Acid → (R)-2-methyl-4,4,4-trifluorobutylamine hydrochloride

Hydrazine monohydrate (3.1 mL) was added to a stirred solution of (R)-2-(2-methyl-4,4,4-trifluorobutyl)-1H-isoindole-1,3(2H)-dione (17.1 g) in anhydrous ethanol (85 mL) and heated to reflux. After three hours' reflux, the solution was cooled; ethanol (40 mL) was added; and the solution was acidified to pH 1 by addition of concentrated hydrochloric acid and was filtered. The filtrate was evaporated, and the residue was purified by sublimation (bath temperature 170° C., at 6.6 Pa) to yield (R)-2-methyl-4,4,4-trifluorobutylamine hydrochloride as a white solid (9.89 g, 88%); mp 187°-191° C.; partial NMR (300 MHz, DMSO-d6, D2O shake): 1.05 (d, 3H, CH3), 2.06-2.36 (m, 2H, CF3CH2) 2.36-2.54 (m, 1H, CHCH3) 2.73 (dd, 1H, CH2N), 2.87 (dd, 1H, CH2N) 8.20 (br s, 2H, NH2).