4'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile → 4'-[3-(3-Hydroxy-3-methyl-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile

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Reaction Steps

The product from Example 154 (130 mg, 0.41 mmol) in dry THF (6 mL) under an atmosphere of nitrogen at 0° C. was treated with a 3.0M solution of methylmagnesium bromide (0.82 mmol). After warming to ambient temperature and stirring for 2 hours, the mixture was quenched with 3 mL of cold saturated ammonium chloride solution and then the solution was partitioned between water (50 mL) and dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (55% yield).

Provenance & Evidence