HCID 19362820, compound → Phenyl acetate

Participants

Reaction Conditions

Reaction Steps

1-Phenyl-2-(4-bromophenyl)ethylamine (6.71 gm, 2.43×10-2 mol) was dissolved in 40 ml of 25% ethyl acetate/ethanol. This solution was then added to a solution of S(-)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (5.69 gm, 2.43×10-2 mol) in 40 ml of 25% ethyl acetate/ethanol. The resulting solution was warmed to 60° C., and then allowed to stand at room temperature for 116 hours. The mixture was then left in a freezer for 24 hours. The resulting white precipitate was collected by vacuum filtration, washed with ethyl ether, and dried in vacuo to yield the desired (-) -α-methoxy-α-trifluoromethyl)phenyl acetate of (-)-1-phenyl-2-(4-bromophenyl)ethylamine (2.93 gm). The mother liquor was concentrated to dryness under reduced pressure, and the residue was crystallized as described above using 60 ml of 25% ethyl acetate/ethanol to yield an additional 0.63 gm of the phenylacetate of (-)-1-phenyl-2-(4-bromophenyl)ethylamine. The combined precipitates (3.56 gm, 57%, mp=143°-145° C.) were treated with 30 ml of 2.5N aqueous NaOH, extracted with three 30 ml portions of dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to yield the desired (-)-1-phenyl-2-(4-bromophenyl)ethylamine as a yellow oil (1.74 gm, 52%), [α]D25 =-62.7 (EtOH), shown to be 99.8% enantiomerically pure by chiral HPLC.

Provenance & Evidence