Ammonium Chloride → 1-Cyclohexyl-3-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one

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Reaction Conditions

Reaction Steps

Dissolve commercially available 1-cyclohexyl-pyrrolidin-2-one (88.2 g, 527.9 mmol) in 2500 mL tetrahydrofuran and cool to −78° C. Add 176 mL 2 M LDA and stir for ˜5 min. Add 2-bromomethyl-1,3-dichloro-5-methoxy-benzene (95 g, 351.9 mmol) and allow the reaction to warm to room temperature. Pour the mixture into saturated ammonium chloride and extract twice with dichloromethane. Dry over sodium sulfate, filter and concentrate under vacuum to obtain a tan solid. Add hexanes and stir rapidly before filtering. Wash the filter cake several times with cold hexane to obtain 86 g (69%) of a light-tan solid: MS (m/z): 356 (M+).

Provenance & Evidence