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0 °C

To a solution of methyl 2-[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]-4,5-dihydro-4-oxazolecarboxylate (i.e. the product of Example 9, Step D) (1.09 g, 3.04 mmol) in 25 mL of dichloromethane at 0° C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (508 mg, 3.34 mmol). Bromotrichloromethane (662 mg, 3.34 mmol) was then added dropwise over 5 minutes. The reaction mixture was stirred for 6 h at 0° C. The reaction mixture was washed with saturated aqueous ammonium chloride (2×50 mL), the aqueous phase was back-extracted with ethyl acetate (2×25 mL), and the combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 50-100% of ethyl acetate in hexanes as eluant to give 600 mg of the title compound as an oil.

1. washThe reaction mixture was washed with saturated aqueous ammonium chloride (2×50 mL)
2. extractionthe aqueous phase was back-extracted with ethyl acetate (2×25 mL)
3. dry with materialthe combined organic layers were dried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by silica gel chromatography