Flurbiprofen → 1-Phenethylamine, (-)-

Participants

Reaction Conditions

Reaction Steps

Racemic flurbiprofen (61.0 g) was dissolved in a mixture of methanol (40 ml) and toluene (160 ml). The mixture was heated to 60° C. and (S)-α-methylbenzylamine 16.9 ml was added over 10 minutes. A seed crystal of (S)-flurbiprofen-(S)-α-methylbenzylamine was added to the reaction mixture which was then cooled to 0° to 5° C., and held at that temperature for one hour. The precipitate was collected by filtration to give a (S)-α-methylbenzylamine salt of (S)-enriched flurbiprofen-(S)-α-methylbenzylamine of an enantiomeric purity of 92.2%. After recrystallisation of the precipitate from a mixture of methanol (48 ml) and toluene (192 ml), a further-(S)-enriched-flurbiprofen-(S)-α-methylbenzylamine of an enantiomeric purity of 98.5% was obtained.

Provenance & Evidence