Potassium Carbonate → 1-(2,2-Diphenylethyl)-3-methylpyrrolidin-3-ol

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Reaction Steps

According to Example 15, 3-methylpyrrolidin-3-ol hydrochloride was synthesized. To a 500 mL reaction flask were added 3-methylpyrrolidin-3-ol hydrochloride (11.46 g, 83 mmol), anhydrous potassium carbonate (28.75 g, 208 mmol) and acetonitrile (220 mL). To the resulting mixture was slowly added a solution of 2,2-diphenylethyl methanesulfonate (23 g, 83 mmol) in acetonitrile dropwisely at 85° C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the resulting mixture was evaporated under reduced pressure to remove acetonitrile. A mixed solution of dichloromethane and water was added for extraction. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce a crude product. The crude product was purified by column chromatography (silica gel column, eluted with petroleum ether:ethyl acetate=30:1 (volumetric ratio)) to produce 1-(2,2-diphenylethyl)-3-methylpyrrolidin-3-ol (13.6 g) in a yield of 58.23%.

Provenance & Evidence