Hydrochloric Acid → (R)-3-methyl-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with (R)-2-methyl-N-((R)-3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butyl)propane-2-sulfinamide (47.5 g, 115.5 mmol) and methanol (300 mL). The mixture was cooled to 0° C. and 2.0N HCl in ether (150 mL) was added. The reaction was stirred for 20 minutes. The reaction was then concentrated under reduced pressure. Trituration with ether provided (R)-3-methyl-1-(4′-(trifluoromethyl)biphenyl-4-yl)butan-1-amine hydrochloride (35.3 g, 89%), as a white solid. 1H NMR (400 MHz, CD3OD, δ): 0.95 (d, 3H) 0.99 (d, J=6.44 Hz, 3H) 1.38-1.51 (m, 1H) 1.78-1.91 (m, 1H) 1.92-2.03 (m, 1H) 4.40 (dd, J=10.15, 5.66 Hz, 1H) 7.56-7.63 (m, 2H) 7.74-7.88 (m, 6H). MS (M+1): 291.2. [α]D=−11.9, c=1.8 (MeOH).

Provenance & Evidence