alpha-(Trifluoromethyl)benzenemethanamine → (alphaR)-alpha-(Trifluoromethyl)benzenemethanamine

Participants

Reaction Steps

L-Tartaric acid (36 g, 240.0 mmol) was added to a solution of 2,2,2-trifluoro-1-phenylethanamine (40 g, 228.57 mmol) in isopropanol (400 mL). The solution was heated to reflux for 30 min. The mixture was cooled and the solid was collected by filtration. The material was diluted with Na2CO3/H2O and the aqueous mixture was extracted with methylene chloride (3×100 mL). The combined organic extracts were dried over K2CO3 and concentrated under reduced pressure to afford (1R)-2,2,2-trifluoro-1-phenylethanamine (12.5 g, 31% yield) as a white solid.

Provenance & Evidence