Dimethyl methylphosphonate → {6-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-2-oxo-hexyl}-phosphonic acid dimethyl ester

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Reaction Steps

A solution of dimethyl methylphosphonate (2.48 g, 20 mmol) in anhydrous THF (30 mL) was cooled to −78° and treated dropwise with 2.5 M n-BuLi (8.0 mL). After stirring at −78° for 45 min, a solution of ester 6-6 (1.85 g, 5.0 mmol) in THF (10 mL) was added dropwise and the resulting solution stirred for 30 min at −78°, quenched with sat. NH4Cl (25 mL), then extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a yellow oil. Chromatography on silica gel (5% MeOH/CH2Cl2) afforded 6-7 as a yellow oil in 89% yield.

Provenance & Evidence