1-Phenethylamine, (+)- → HCID 86638377, compound

Participants

Reaction Steps

A solution of (R)-(+)-1-phenylethylamine (104 mg, 0.86 mmol) in diisopropyl ether/MeOH 20:1 (4.5 mL) was added dropwise at RT to a solution of 2-(3-chloro-4-trifluoromethyl-phenylamino)-propionic acid (417 mg, 1.56 mmol) in diisopropyl ether/MeOH 20:1 (4.5 mL), then after 2 h the precipitate was collected by filtration, washed with diisopropyl ether, and dried under vacuum. This material was digested in chloroform (3 mL) at 50° C. for 18 h, then collected by filtration, and dried under vacuum to afford 2-(3-chloro-4-trifluoromethyl-phenylamino)-propionic acid (R)-(+)-1-phenylethylamine salt (187 mg). This salt was partitioned between 10% aq. KHSO4 solution and EtOAc. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (134 mg, 32%) in an enantiomeric ratio of 98.5:1.5. White solid.

Provenance & Evidence