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Gram scale crystallization was also examined. A toluene solution (50 mL) containing 1c (5.0 g) and DBU (20 mol%) was stirred in a flask at 1008C until 1c was gradually crystallized and all solvent evaporated. After DBU was removed, the enantiomeric excess of 1c was analyzed by HPLC, and was shown to be 93% ee. It was revealed that the total spontaneous resolution could be applied for large scale crystallization
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Gram scale crystallization was also examined. A toluene solution (50 mL) containing 1c (5.0 g) and DBU (20 mol%) was stirred in a flask at 1008C until 1c was gradually crystallized and all solvent evaporated. After DBU was removed, the enantiomeric excess of 1c was analyzed by HPLC, and was shown to be 93% ee. It was revealed that the total spontaneous resolution could be applied for large scale crystallization.
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41
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Optically active solid of 1d (10% ee or 20% ee, 0.50 g, 1.98 mmol) was suspended in hexane (10.0 mL) with 1.0 g of glass beads (2 mm) and was stirred in the presence of DBU (0.06 g, 0.40 mmol) for 12 h. The enantiomeric excess of the crystalline solid was measured and found to be racemic in both cases
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Optically active solid of 1d (10% ee or 20% ee, 0.50 g, 1.98 mmol) was suspended in hexane (10.0 mL) with 1.0 g of glass beads (2 mm) and was stirred in the presence of DBU (0.06 g, 0.40 mmol) for 12 h. The enantiomeric excess of the crystalline solid was measured and found to be racemic in both cases.
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