1-Phenethylamine, (-)- → (S)-Ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-oxocyclohexane carboxylate (6, 484.9 g) and (S)-(−)-1-phenylethylamine (7, 362.5 g) were charged into an RB flask followed by heptanes (1.5 L) and Ytterbium (III) trifluoromethane sulfonate (8.8 g). The contents were heated to reflux for 3 hours and the liberated water was removed simultaneously and then cooled to 22° C. (±3° C.). The insoluble material was filtered and the filtrate was concentrate on a rotary evaporator under vacuum to afford 869.4 g of (S)-ethyl 2-(1-phenylethylamino)cyclohex-1-enecarboxylate (8) as an oil.

Provenance & Evidence