Dimethylformamide → (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate

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Reaction Steps

To a solution of (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-ylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate methyliodide (7 g, 12 mmol) in CH2Cl2 (70 mL) was added 60% NaH in oil (580 mg, 14 mmol). After 5 minutes, DMF (7 mL) was added and the mixture stirred at ambient temperature for 1 hour. The mixture was poured into saturated ammonium chloride (70 mL) and the solution was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting oil was triturated with ether (100 mL) and the ether layer was washed with brine. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to yield (S)-tert-butyl 1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-ylcarbamate (3.2 g, 8.2 mmol, 68%).

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