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The preparative resolution by preferential crystallization (PC) of proxyphylline has been achieved despite the existence of a stable racemic compound. This is enabled through the careful selection of a solvent in which both the racemic compound and the metastable conglomerate possess a low nucleation rate. Induction time measurements in isobutyl alcohol show that a highly supersaturated solution ( = 2.3) remains clear for almost 1 hour at 20 mL scale, revealing a slow nucleation rate. Afterdoi:10.1021/acs.molpharmaceut.9b00805.s001 fatcat:lob6mhglgnadriztxjlt42b5ji