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A solution of sodium 4-(4-pyridyl)benzoate (500 mg, 2.26 mmol), and N-methylmorpholine (0.250 mL, 2.26 mmol) in tetrahydrofuran (12 mL) was treated with ethyl chloroformate (0.216 mL, 2.26 mmol). After 0.25 h, the mixture was treated with sodium borohydride (256 mg, 6.79 mmol) followed by methanol (24 mL) dropwise. After 0.5 h, the mixture was treated with 10% aqueous acetic acid and concentrated in vacuo. The residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide. The aqueous layer was extracted twice with ethyl acetate and the combined extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo to yield 140 mg of the title compound which was used without further purification.

1. waitAfter 0.5 h
2. concentrationconcentrated in vacuo
3. customThe residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
4. extractionThe aqueous layer was extracted twice with ethyl acetate
5. dry with materialthe combined extracts were dried (magnesium sulfate)
6. filtrationfiltered
7. concentrationconcentrated in vacuo