Ethanol → (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (2R,3R)-2,3-bis(benzoyloxy) succinate

Participants

Reaction Steps

A solution of (−)-dibenzoyl-L-tartaric acid monohydrate (2.11 g, 5.89 mmol, 1.0 equiv) in ethanol (22 mL) was added to (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (III) (5.88 mmol, 1.0 equiv) dissolved in ethanol (22 mL) at 20° C. Solids precipitated and the mixture was granulated 18 hours. The light yellow solids filtered from the mixture were washed with ethanol and dried on the filter, giving (S)-3-bromo-5-(1-methylpyrrolidin-2-yl)pyridine (2R,3R)-2,3-bis (benzoyloxy) succinate (IIIB) (2.9556 g, 84%, 99.5% ee).

Provenance & Evidence