Sulfuric Acid → (2R)-4-(3-pyridyl)-1,2-butanediol

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Reaction Steps

Under argon gas, MeOH (70 mL) was added to 10% palladium-on-carbon (1.0 g). Then, the (2R)-1-O-benzyl-4-(3-pyridyl)-1,2-butanediol produced in Example 3 (28.25 g, 100 mmol) and sulfuric acid (19.6 g, 200 mmol) were added. After degassing under reduced pressure, a hydrogen atmosphere was established. The pressure was increased to 3 atm. and the mixture was stirred at room temperature for 16 hours. The palladium-on-carbon was filtered off and the solvent was distilled off under reduced pressure, whereupon a light-yellow oil was obtained. To this oil was added a saturated aqueous solution of sodium hydrogencarbonate for neutralization, followed by concentration under reduced pressure. The residue was extracted with ethyl acetate twice (200 mL each). The organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the oily residue was purified by silica gel column chromatography (Merck's Kieselgel 60, MeOH/ethyl acetate=1/9) to give 10.52 g (isolation yield: 63%) of (2R)-4-(3-pyridyl)-1,2-butanediol (yellow oil).

Provenance & Evidence